TWI394805B - Disperse dyes, disperse dye compositions, ink for inkjet printing and dyeing, dyeing methods using the same, and dyeing methods - Google Patents
Disperse dyes, disperse dye compositions, ink for inkjet printing and dyeing, dyeing methods using the same, and dyeing methods Download PDFInfo
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- TWI394805B TWI394805B TW95142383A TW95142383A TWI394805B TW I394805 B TWI394805 B TW I394805B TW 95142383 A TW95142383 A TW 95142383A TW 95142383 A TW95142383 A TW 95142383A TW I394805 B TWI394805 B TW I394805B
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P5/00—Other features in dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form
- D06P5/30—Ink jet printing
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B29/00—Monoazo dyes prepared by diazotising and coupling
- C09B29/06—Monoazo dyes prepared by diazotising and coupling from coupling components containing amino as the only directing group
- C09B29/08—Amino benzenes
- C09B29/0805—Amino benzenes free of acid groups
- C09B29/0807—Amino benzenes free of acid groups characterised by the amino group
- C09B29/0809—Amino benzenes free of acid groups characterised by the amino group substituted amino group
- C09B29/0811—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino
- C09B29/0823—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN
- C09B29/0826—Amino benzenes free of acid groups characterised by the amino group substituted amino group further substituted alkylamino, alkenylamino, alkynylamino, cycloalkylamino aralkylamino or arylamino substituted by CN having N(-alkenylene/-alkynylene-O)(-alkenylene/-alkynylene-CN)
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0041—Blends of pigments; Mixtured crystals; Solid solutions mixtures containing one azo dye
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B67/00—Influencing the physical, e.g. the dyeing or printing properties of dyestuffs without chemical reactions, e.g. by treating with solvents grinding or grinding assistants, coating of pigments or dyes; Process features in the making of dyestuff preparations; Dyestuff preparations of a special physical nature, e.g. tablets, films
- C09B67/0033—Blends of pigments; Mixtured crystals; Solid solutions
- C09B67/0046—Mixtures of two or more azo dyes
- C09B67/0051—Mixtures of two or more azo dyes mixture of two or more monoazo dyes
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
- D06P1/16—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using dispersed, e.g. acetate, dyestuffs
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
- D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
- D06P3/34—Material containing ester groups
- D06P3/52—Polyesters
- D06P3/54—Polyesters using dispersed dyestuffs
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- Coloring (AREA)
- Inks, Pencil-Leads, Or Crayons (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Ink Jet Recording Methods And Recording Media Thereof (AREA)
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Description
本發明係關於一種新穎之橙色分散性染料、分散性染料組成物、噴墨印染用墨水、與使用其等之染色方法及染色物,該橙色分散性染料,對疏水性纖維材料之染色性優異、具有高耐光堅牢度、昇華堅牢度亦優異、且兼具良好之上色染深性,而特別適用於汽車內裝用片所使用之染料。The present invention relates to a novel orange disperse dye, a disperse dye composition, an ink for inkjet printing, a dyeing method using the same, and a dyeing product which is excellent in dyeability to a hydrophobic fiber material. It has high light fastness, excellent sublimation fastness, good dyeing and deep dyeing, and is especially suitable for dyes used in automotive interiors.
近年來,漸漸使用疏水性纖維材料做為汽車內裝用、特別是座椅片之材質,特別常使用聚酯系纖維。又,近年來由於時尚性之提升亦要求豐富的色彩。然而,當為汽車內裝用片時,由於高溫長時間之曝光,黃色產生變色、褪色,且亦為紅色及藍色之混合染色物之變色原因。In recent years, hydrophobic fiber materials have been gradually used as materials for automobile interiors, particularly seat panels, and polyester fibers are often used. In addition, in recent years, due to the improvement of fashion, it also requires rich colors. However, when it is used for the interior of a car, the yellow color is discolored and faded due to exposure to high temperature for a long time, and it is also a cause of discoloration of the mixed dye of red and blue.
一般之耐光性之評價方法,係根據JIS L 0842之試驗方法,而汽車內裝用片所使用之染料的耐光性評價方法,則有更為嚴苛之試驗方法、亦即使用氙弧燈之加速試驗法(例如,豐田法)。若使用該試驗方法,較一般試驗方法更能使耐光性差之染料與良好之染料顯現顯著之差。The general evaluation method of light resistance is based on the test method of JIS L 0842, and the light resistance evaluation method of the dye used for the automobile interior sheet has a more severe test method, that is, using a xenon arc lamp. Accelerated test method (for example, the Toyota Law). If the test method is used, the dye having poor light resistance is significantly worse than the good dye than the general test method.
做為因高溫長時間曝光而黃色變色、褪色現象之對策,例如,曾於下述專利文獻1、專利文獻2、專利文獻3等提出一種高耐光性黃色分散性染料組成物。For example, a high light-resistant yellow disperse dye composition has been proposed in the following Patent Document 1, Patent Document 2, and Patent Document 3, as a countermeasure for yellow discoloration and fading.
然而,將該專利文獻1~3所記載之黃色分散性染料組成物做為紅色及藍色之配合成分使用,欲得到茶色、深藍色或黑色之染色物時,雖具有高耐光堅牢度,但有染色性差之問題。However, the yellow disperse dye composition described in Patent Documents 1 to 3 is used as a component of red and blue, and when it is desired to obtain a dyed substance of brown, dark blue or black, it has high light fastness, but There is a problem of poor dyeability.
因此,茶色、深藍色或黑色用分散性染料之配合成分係使用橙色系染料。以往之橙色系染料,一般係廣泛使用例如下述式(1)之染料或下述式(2)之染料等。Therefore, an orange dye is used as a component of the discolored dye for brown, dark blue or black. In the conventional orange dye, for example, a dye of the following formula (1) or a dye of the following formula (2) is widely used.
然而,上述橙色系染料做為汽車內裝用片之染料使用時,耐光性不足夠,而無法使用於與高耐光性分散性染料進行調色之用途。However, when the above-mentioned orange-based dye is used as a dye for an automobile interior sheet, light resistance is insufficient, and it cannot be used for coloring with a high light-resistant disperse dye.
又,耐光性較佳之橙色系染料,曾提出專利文獻4之實施例1所記載之下述式(3)之染料、及專利文獻5之下述式(4)之染料。Further, the dye of the following formula (3) described in Example 1 of Patent Document 4 and the dye of the following formula (4) of Patent Document 5 have been proposed for the orange-based dye which is excellent in light resistance.
然而,上述式(3)之染料,雖耐光性非常優異,但昇華堅牢度不佳、上色染深性亦有問題。又,上述式(4)之染料,雖上色染深性非常優異,但昇華堅牢度不佳,且做為汽車內裝用片之染料使用時耐光性不足。However, the dye of the above formula (3) is excellent in light fastness, but the sublimation fastness is not good, and the dyeing depth is also problematic. Further, the dye of the above formula (4) is excellent in dyeing depth, but the sublimation fastness is not good, and the light resistance is insufficient when used as a dye for an automobile interior sheet.
專利文獻1:日本特開平6-345989號公報專利文獻2:日本特開平6-166828號公報專利文獻3:日本特開2001-342375號公報專利文獻4:日本特開昭63-135455號公報專利文獻5:日本特開2001-98177號公報,申請專利範圍第2項,式(108)Patent Document 1: Japanese Laid-Open Patent Publication No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. No. Hei. Document 5: Japanese Laid-Open Patent Publication No. 2001-98177, the second application of the patent scope, the formula (108)
本發明為解決上述以往之問題,其課題在於提供一種新穎之橙色分散性染料及使用其之黃色~橙色、茶色、深藍色、黑色用分散性染料組成物、噴墨印染用墨水、與使用其等之染色方法及染色物,該橙色分散性染料,對疏水性纖維材料之染色性優異、具有高耐光堅牢度、昇華堅牢度亦優異、且兼具良好之上色染深,而特別適用於汽車內裝用片所使用之染料。The present invention has been made to solve the above problems, and an object of the present invention is to provide a novel orange disperse dye, a disperse dye composition for yellow to orange, brown, cyan, and black, ink for inkjet printing, and use thereof. The dyeing method and the dyeing material, the orange disperse dye is excellent in dyeability to a hydrophobic fiber material, has high light fastness, excellent sublimation fastness, and good dyeing depth, and is particularly suitable for use in dyeing. Dyes used in automotive interiors.
本發明之橙色分散性染料,其特徵在於,以下述式[1]所表示。The orange disperse dye of the present invention is represented by the following formula [1].
[上述式[1]中,X1 表示氯原子或溴原子,R1 表示苯甲醯基、氰乙基、C1 ~C4 烷基、苯基或以C1 ~C4 烷基取代1個以上之苯基。][In the above formula [1], X 1 represents a chlorine atom or a bromine atom, and R 1 represents a benzamidine group, a cyanoethyl group, a C 1 -C 4 alkyl group, a phenyl group or a C 1 -C 4 alkyl group; More than one phenyl group. ]
又,本發明之黃色~橙色系分散性染料組成物(以下,稱為「第1分散性染料組成物」),其特徵在於,含有上述式[1]所表示之橙色分散性染料,及與選自下述式[2]所表示之染料、下述式[3]所表示之染料、下述式[4]所表示之染料、下述式[5]所表示之染料、及下述式[6]所表示之染料中之至少一種黃色系染料。Further, the yellow-orange disperse dye composition of the present invention (hereinafter referred to as "first disperse dye composition") is characterized by containing the orange disperse dye represented by the above formula [1], and a dye represented by the following formula [2], a dye represented by the following formula [3], a dye represented by the following formula [4], a dye represented by the following formula [5], and the following formula: [6] At least one of the dyes represented by the yellow dye.
[上述式[4]中,X2 表示氫原子或溴原子,R2 表示氫原子或-COOC2 H4 OC2 H5 基。][In the above formula [4], X 2 represents a hydrogen atom or a bromine atom, and R 2 represents a hydrogen atom or a -COOC 2 H 4 OC 2 H 5 group. ]
[上述式[6]中,R3 表示C1 ~C4 烷基、苯基或以C1 ~C4 烷基取代1個以上之苯基。][In the above formula [6], R 3 represents a C 1 -C 4 alkyl group, a phenyl group or a phenyl group substituted with one or more C 1 -C 4 alkyl groups. ]
又,本發明之分散性染料組成物(以下,稱為「第2分散性染料組成物」),其特徵在於,含有上述式[1]所表示之橙色分散性染料、與下述式[17]所表示之染料。In addition, the disperse dye composition of the present invention (hereinafter referred to as "the second disperse dye composition") contains the orange disperse dye represented by the above formula [1] and the following formula [17] ] the dye represented.
又,本發明之分散性染料組成物(以下,稱為「第3分散性染料組成物」),其特徵在於,含有上述式[1]所表示之橙色分散性染料或上述黃色~橙色系分散性染料組成物之1種之第1配合用橙色系分散性染料組成物,及選自下述式[7]所表示之染料、下述式[8]所表示之染料、下述式[9]所表示之染料、下述式[10]所表示之染料、及下述式[11]所表示之染料中之至少1種紅色系染料,及選自下述式[12]所表示之染料、下述式[13]所表示之染料、下述式[14]所表示之染料、下述式[15]所表示之染料、及下述式[16]所表示之染料中之至少1種藍色系染料。Further, the disperse dye composition of the present invention (hereinafter referred to as "the third disperse dye composition") is characterized by containing the orange disperse dye represented by the above formula [1] or the yellow-orange dispersion described above. The orange-based disperse dye composition for the first compound of the first dye composition, and the dye represented by the following formula [7], the dye represented by the following formula [8], and the following formula [9] a dye represented by the formula, a dye represented by the following formula [10], and at least one red dye of the dye represented by the following formula [11], and a dye selected from the following formula [12] a dye represented by the following formula [13], a dye represented by the following formula [14], a dye represented by the following formula [15], and at least one of the dyes represented by the following formula [16] Blue dye.
[上述式[8]中,R4 表示氫原子、-OCH3 基、-OC2 H5 或-SO2 NHC3 H6 OC2 H5 基。][In the above formula [8], R 4 represents a hydrogen atom, -OCH 3 group, -OC 2 H 5 or -SO 2 NHC 3 H 6 OC 2 H 5 group. ]
[上述式[10]中,R5 表示苯基、以C1 ~C4 烷基取代1個以上之苯基、-COOC2 H5 基或-COOC6 H5 基。][In the above formula [10], R 5 represents a phenyl group, a C 1 -C 4 alkyl group substituted with one or more phenyl groups, a -COOC 2 H 5 group or a -COOC 6 H 5 group. ]
[上述式[11]中,R6 表示氫原子、-CH3 基或-C2 H5 基。][In the above formula [11], R 6 represents a hydrogen atom, a -CH 3 group or a -C 2 H 5 group. ]
[上述式[13]中,R7 表示-C3 H6 OCH3 基或-C3 H6 OC2 H4 OCH3 基。][In the above formula [13], R 7 represents a -C 3 H 6 OCH 3 group or a -C 3 H 6 OC 2 H 4 OCH 3 group. ]
[上述式[15]中,R8 表示羥基、-OCH3 基或-OC2 H5 基。][In the above formula [15], R 8 represents a hydroxyl group, an -OCH 3 group or an -OC 2 H 5 group. ]
[上述式[16]中,X3 表示氫原子或溴原子。][In the above formula [16], X 3 represents a hydrogen atom or a bromine atom. ]
又,該第1配合用橙色系分散性染料組成物,係指於該黃色~橙色系之第1分散性染料組成物,含有該橙色分散性染料65~98重量%、及該黃色系染料2~35重量%,為橙色系、且為配合用。In addition, the yellow-orange-based first disperse dye composition is contained in the yellow-orange-based first disperse dye composition, and the orange disperse dye is contained in an amount of 65 to 98% by weight and the yellow dye 2 ~35 wt%, is orange, and is used in combination.
又,本發明之分散性染料組成物(以下,稱為「第4分散性染料組成物」),其特徵在於,含有:上述第2分散性染料組成物之1種之第2配合用橙色系分散性染料組成物,及選自上述式[7]所表示之染料、上述式[8]所表示之染料、上述式[9]所表示之染料、上述式[10]所表示之染料、及上述式[11]所表示之染料中之至少1種紅色系染料,及選自上述式[12]所表示之染料、上述式[13]所表示之染料、上述式[14]所表示之染料、上述式[15]所表示之染料、及上述式[16]所表示之染料中之至少1種藍色系染料。又,該第2配合用橙色系分散性染料組成物,係指於該第2分散性染料組成物中,含有該橙色分散性染料20~80重量%、及上述式[17]所表示之染料20~80重量%,且為橙色系、且為配合用。Furthermore, the disperse dye composition of the present invention (hereinafter referred to as "the fourth disperse dye composition") is characterized in that it contains one of the second disperse dye compositions and the second compound orange a disperse dye composition, a dye represented by the above formula [7], a dye represented by the above formula [8], a dye represented by the above formula [9], a dye represented by the above formula [10], and At least one red dye of the dye represented by the above formula [11], and a dye selected from the above formula [12], a dye represented by the above formula [13], and a dye represented by the above formula [14] Further, at least one of the dyes represented by the above formula [15] and the dyes represented by the above formula [16] is a blue dye. In addition, the second disperse dye composition according to the second formula contains 20 to 80% by weight of the orange disperse dye and the dye represented by the above formula [17]. 20 to 80% by weight, and is orange, and is used in combination.
本發明之疏水性纖維材料之染色方法,其特徵在於,使用上述橙色分散性染料、上述第1至第4分散性染料組成物或上述第1或第2配合用橙色系分散性染料組成物。In the method for dyeing a hydrophobic fibrous material of the present invention, the orange dispersible dye, the first to fourth disperse dye compositions, or the first or second orange disperse dye composition for blending is used.
本發明之噴墨印染用墨水,其特徵在於,含有上述橙色分散性染料、上述第1至第4分散性染料組成物或上述第1或第2配合用橙色系分散性染料組成物。The ink for inkjet printing of the present invention comprises the orange disperse dye, the first to fourth disperse dye compositions, or the first or second orange disperse dye composition.
本發明之橙色分散性染料、分散性染料組成物、及噴墨印染用墨水,於疏水性纖維材料之染色,上色染深性等染色性優異、昇華堅牢度亦優異、且特別適於要求高耐光堅牢度之汽車內裝用片之染色。又,亦可提供使用其等之染色方法及染色物。The orange disperse dye, the disperse dye composition, and the ink for inkjet printing of the present invention are excellent in dyeability, dyeing depth, and the like, and excellent in sublimation fastness, and are particularly suitable for the dyeing of the hydrophobic fiber material. Dyeing of automotive interiors with high light fastness. Further, a dyeing method and a dyed product using the same can be provided.
本發明之橙色分散性染料,如上述,係上述式[1]所表示之橙色分散性染料。The orange disperse dye of the present invention, as described above, is an orange disperse dye represented by the above formula [1].
[上述式[1]中,X1 表示氯原子或溴原子,R1 表示苯甲醯基、氰乙基、C1 ~C4 烷基、苯基或以C1 ~C4 烷基取代1個以上之苯基。][In the above formula [1], X 1 represents a chlorine atom or a bromine atom, and R 1 represents a benzamidine group, a cyanoethyl group, a C 1 -C 4 alkyl group, a phenyl group or a C 1 -C 4 alkyl group; More than one phenyl group. ]
本說明書中,該C1 ~C4 烷基,係指碳數1~4之直鏈狀或具支鏈之烷基之意,可舉例如甲基、乙基、丙基、異丙基、正丁基、二級丁基、三級丁基等。該C1 ~C4 烷基,較佳為正丁基。In the present specification, the C 1 -C 4 alkyl group means a linear or branched alkyl group having 1 to 4 carbon atoms, and examples thereof include a methyl group, an ethyl group, a propyl group, and an isopropyl group. N-butyl, secondary butyl, tertiary butyl and the like. The C 1 -C 4 alkyl group is preferably n-butyl.
又,該以C1 ~C4 烷基取代1個以上之苯基,可舉例如於苯基被1~5個C1 ~C4 烷基所取代者。當該苯基之以2個以上之C1 ~C4 烷基取代時,該烷基可分別不同或相同。該取代苯基,可舉例如4-甲基苯基、2,4-二甲基苯基、4-乙基苯基、2,4,6-三甲基苯基等。Further, the phenyl group may be substituted with one or more C 1 -C 4 alkyl groups, and for example, the phenyl group may be substituted with 1 to 5 C 1 -C 4 alkyl groups. When the phenyl group is substituted with two or more C 1 -C 4 alkyl groups, the alkyl groups may be different or the same. The substituted phenyl group may, for example, be 4-methylphenyl, 2,4-dimethylphenyl, 4-ethylphenyl or 2,4,6-trimethylphenyl.
上述式[1]所表示之橙色分散性染料,可舉例如,上述式[1]中,X1 表示氯原子、R1 表示苯甲醯基者、X1 表示氯原子、R1 表示氰乙基者、X1 表示氯原子、R1 表示C1 ~C4 烷基者、X1 表示氯原子、R1 表示苯基者、X1 表示氯原子、R1 表示以C1 ~C4 烷基取代1個以上之苯基者、X1 表示溴原子、R1 表示苯甲醯基者、X1 表示溴原子、R1 表示氰乙基者、X1 表示溴原子、R1 表示C1 ~C4 烷基者、X1 表示溴原子、R1 表示苯基者、X1 表示溴原子、R1 表示以C1 ~C4 烷基取代1個以上之苯基者。In the orange disperse dye represented by the above formula [1], for example, in the above formula [1], X 1 represents a chlorine atom, R 1 represents a benzamidine group, X 1 represents a chlorine atom, and R 1 represents a cyanoethane group. The base, X 1 represents a chlorine atom, R 1 represents a C 1 -C 4 alkyl group, X 1 represents a chlorine atom, R 1 represents a phenyl group, X 1 represents a chlorine atom, and R 1 represents a C 1 -C 4 alkane. When one or more phenyl groups are substituted, X 1 represents a bromine atom, R 1 represents a benzamidine group, X 1 represents a bromine atom, R 1 represents a cyanoethyl group, X 1 represents a bromine atom, and R 1 represents a C 1 group. In the case of ~C 4 alkyl group, X 1 represents a bromine atom, R 1 represents a phenyl group, X 1 represents a bromine atom, and R 1 represents a group in which one or more phenyl groups are substituted by a C 1 -C 4 alkyl group.
上述式[1]所表示之橙色分散性染料,較佳為,上述式[1]中,X1 表示氯原子、R1 表示苯甲醯基者、及X1 表示氯原子、R1 表示氰乙基者,更佳為,上述式[1]中,X1 表示氯原子、R1 表示苯甲醯基者。In the orange disperse dye represented by the above formula [1], in the above formula [1], X 1 represents a chlorine atom, R 1 represents a benzamidine group, and X 1 represents a chlorine atom, and R 1 represents a cyanogen. In the above formula [1], X 1 represents a chlorine atom, and R 1 represents a benzamidine group.
於本發明,上述式[1]之較佳具體例,可舉例如,上述式[1]中,X1 表示氯原子、R1 表示苯甲醯基之下述式[1-1]所表示之染料;上述式[1]中,X1 表示溴原子、R1 表示氰乙基之下述式[1-2]所表示之染料;及上述式[1]中,X1 表示溴原子、R1 表示C4 烷基之下述式[1-3]所表示之染料。In a preferred embodiment of the above formula [1], in the above formula [1], X 1 represents a chlorine atom, and R 1 represents a benzamidine group represented by the following formula [1-1]. In the above formula [1], X 1 represents a bromine atom, R 1 represents a cyanoethyl group represented by the following formula [1-2]; and in the above formula [1], X 1 represents a bromine atom, R 1 represents a dye represented by the following formula [1-3] of a C 4 alkyl group.
上述染料之中,由耐光性的觀點考量,特別以[1-1]之染料為佳。Among the above dyes, from the viewpoint of light resistance, a dye of [1-1] is particularly preferable.
以下,說明上述式[1]所表示之橙色分散性染料之製造方法。首先,將下述式[100]之化合物,於無機酸或有機羧酸中,於視情況所追加之水的存在下,使用亞硝化劑或亞硝基硫酸進行重氮化而製得重氮化合物。所使用之有機羧酸,可舉例如乙酸及丙酸。又,礦酸,可舉例如鹽酸、磷酸及硫酸,較佳為硫酸。所使用之亞硝化劑,係鹼金屬之亞硝酸鹽,例如,固體狀態或水溶液狀態之亞硝酸鈉。重氮化溫度,較佳為-5~30℃、更佳為0~20℃。Hereinafter, a method for producing the orange disperse dye represented by the above formula [1] will be described. First, a compound of the following formula [100] is subjected to diazotization using a nitrosating agent or nitrosylsulfuric acid in an inorganic acid or an organic carboxylic acid in the presence of water added as the case may be, to obtain a diazo Compound. The organic carboxylic acid to be used may, for example, be acetic acid or propionic acid. Further, the mineral acid may, for example, be hydrochloric acid, phosphoric acid or sulfuric acid, preferably sulfuric acid. The nitrosating agent used is an alkali metal nitrite such as sodium nitrite in a solid state or in an aqueous solution state. The diazotization temperature is preferably -5 to 30 ° C, more preferably 0 to 20 ° C.
[上述式[100]中,X1 表示氯原子或溴原子。][In the above formula [100], X 1 represents a chlorine atom or a bromine atom. ]
於做為偶合劑之下述式[101]所表示化合物之溶液或懸浮液中,將所得之重氮化合物之溶液,於例如0~35℃之溫度範圍添加,製得上述式[1]所表示之化合物。最初所導入之偶合劑溶液或懸浮液之pH以弱酸性為佳。又,亦可將做為偶合劑之下述式[101]所表示之化合物,加入如乙酸等弱酸溶液中作成溶解狀態或懸浮狀態,再將重氮化合物之溶液添加於其。於此場合,添加乙酸鈉等緩衝劑會有較有利之情形。In the solution or suspension of the compound represented by the following formula [101] as a coupling agent, the solution of the obtained diazo compound is added at a temperature of, for example, 0 to 35 ° C to obtain the above formula [1]. Expressed as a compound. The pH of the initially introduced coupling agent solution or suspension is preferably weakly acidic. Further, a compound represented by the following formula [101] which is a coupling agent may be added to a weak acid solution such as acetic acid to be dissolved or suspended, and a solution of a diazo compound may be added thereto. In this case, it may be advantageous to add a buffer such as sodium acetate.
[上述式[101]中,R1 表示苯甲醯基、氰乙基、C1 ~C4 烷基、苯基或以C1 ~C4 烷基取代1個以上之苯基。][In the above formula [101], R 1 represents a benzamidine group, a cyanoethyl group, a C 1 -C 4 alkyl group, a phenyl group or a phenyl group substituted with one or more C 1 -C 4 alkyl groups. ]
又,上述式[1]之重氮化合物之原料之下述式[100]所表示之化合物,係美國專利第3342804號說明書之染料(IV)之重氮成分,而為周知者。Further, the compound represented by the following formula [100] of the raw material of the diazo compound of the above formula [1] is a diazo component of the dye (IV) of the specification of U.S. Patent No. 3,342,804, and is known.
又,上述式[101]所表示之化合物之中,當R1 為苯甲醯基時,例如,係使用一般廣為所知之C.I.Disperse Orange 73之偶合劑。Further, among the compounds represented by the above formula [101], when R 1 is a benzamidine group, for example, a coupling agent of CIDisperse Orange 73 which is generally known is used.
又,R1 為氰乙基、丁基之式[101]所表示之化合物,亦為一般廣為所知而使用之周知化合物,而可以習知之方法合成。Further, a compound represented by the formula [101] wherein R 1 is a cyanoethyl group or a butyl group is also a known compound which is generally known and used, and can be synthesized by a conventional method.
本發明人等,努力深入探討的結果而驚訝地發現,上述式[1]所表示之染料,係對疏水性纖維材料之染色性優異、具有高耐光堅牢度、昇華堅牢度亦優異、且兼具良好之上色染深性、而特別適用於汽車內裝用片用染料之橙色分散性染料,而完成本發明。As a result of intensive investigation, the present inventors have surprisingly found that the dye represented by the above formula [1] is excellent in dyeability to a hydrophobic fibrous material, has high light fastness, and excellent sublimation fastness, and The present invention has been completed by an orange disperse dye which is excellent in coloring and deep, and is particularly suitable for use in a dye for sheeting for automotive interiors.
上述式[1]所表示之橙色分散性染料,於單獨使用時,即使根據上述豐田法之試驗方法亦具有良好之耐光堅牢度、且升華堅牢度、上色染深性皆優異。The orange disperse dye represented by the above formula [1], when used alone, has excellent light fastness, sublimation fastness, and color deepness even according to the test method of the above-mentioned Toyota method.
因此,藉由與其他高耐光性分散性染料配合,可提供黃色至橙色、茶色、深藍色、黑色用染料組成物。Therefore, by blending with other high light-resistant disperse dyes, a dye composition for yellow to orange, brown, dark blue, and black can be provided.
以下,說明將本發明之橙色分散性染料與黃色系染料配合之黃色~橙色系之第1分散性染料組成物。Hereinafter, a yellow-orange first disperse dye composition in which the orange disperse dye of the present invention and a yellow dye are blended will be described.
由於本發明之橙色分散性染料係稍微帶點紅色,故即使混合少量黃色染料亦可作成帶紅色之黃色。又,藉由該變該等之配合比例,可得黃色至橙色系之各種色相。Since the orange disperse dye of the present invention is slightly reddish, it can be made into a reddish yellow color even if a small amount of yellow dye is mixed. Further, by changing the blending ratio of the above, various hue of yellow to orange color can be obtained.
為了維持耐光性,所配合之黃色系染料亦必須兼具相同之堅牢度,故係使用上述式[2]所表示之染料、上述式[3]所表示之染料、上述式[4]所表示之染料、上述式[5]所表示之染料、及上述式[6]所表示之黃色系染料。In order to maintain the light resistance, the yellow dye to be blended must have the same fastness, and the dye represented by the above formula [2], the dye represented by the above formula [3], and the above formula [4] are used. The dye, the dye represented by the above formula [5], and the yellow dye represented by the above formula [6].
本發明之黃色~橙色系之第1分散性染料組成物之中,黃色系分散性染料組成物,較佳為,含有上述式[1]所表示之橙色分散性染料3~20重量%、及選自上述式[2]所表示之染料、上述式[3]所表示之染料、上述式[4]所表示之染料、上述式[5]所表示之染料、及上述式[6]所表示之染料中之至少一種黃色系染料80~97重量%。更佳為,該黃色系分散性染料組成物,含有該橙色分散性染料3~15重量%、及該黃色系染料85~97重量%。In the yellow-orange-based first disperse dye composition of the present invention, the yellow disperse dye composition preferably contains 3 to 20% by weight of the orange disperse dye represented by the above formula [1], and a dye represented by the above formula [2], a dye represented by the above formula [3], a dye represented by the above formula [4], a dye represented by the above formula [5], and a formula represented by the above formula [6] At least one of the dyes of the dye is 80 to 97% by weight. More preferably, the yellow disperse dye composition contains 3 to 15% by weight of the orange disperse dye and 85 to 97% by weight of the yellow dye.
本發明之黃色~橙色系之第1分散性染料組成物之中,橙色系分散性染料組成物,較佳為,含有上述式[1]所表示之橙色分散性染料20~98重量%、及選自上述式[2]所表示之染料、上述式[3]所表示之染料、上述式[4]所表示之染料、上述式[5]所表示之染料、及上述式[6]所表示之染料中之至少一種黃色系染料2~80重量%。更佳為,該橙色分散性染料為25~85重量%、該黃色系染料為15~75重量%,再更佳為,該橙色分散性染料為30~70重量%、該黃色系染料為70~30重量%。In the yellow-orange-based first disperse dye composition of the present invention, the orange-based disperse dye composition preferably contains 20 to 98% by weight of the orange disperse dye represented by the above formula [1], and a dye represented by the above formula [2], a dye represented by the above formula [3], a dye represented by the above formula [4], a dye represented by the above formula [5], and a formula represented by the above formula [6] At least one of the dyes of the dye is 2 to 80% by weight. More preferably, the orange disperse dye is 25 to 85% by weight, the yellow dye is 15 to 75% by weight, and more preferably, the orange disperse dye is 30 to 70% by weight, and the yellow dye is 70. ~30% by weight.
又,上述式[17]之染料亦為耐光性良好之染料故可配合使用。藉由與上述式[1]所表示之橙色分散性染料併用,可改善該式[17]之染料之缺點之昇華堅牢度及上色染深性。因此,本發明之第2分散性染料組成物,其特徵在於,含有上述式[1]所表示之橙色分散性染料、與上述式[17]所表示之染料。Further, the dye of the above formula [17] is also a dye having good light resistance and can be used in combination. By using in combination with the orange disperse dye represented by the above formula [1], the sublimation fastness and the dyeing darkness of the disadvantage of the dye of the formula [17] can be improved. Therefore, the second disperse dye composition of the present invention contains the orange disperse dye represented by the above formula [1] and the dye represented by the above formula [17].
本發明之橙色系之第2分散性染料組成物,較佳為,含有上述式[1]所表示之橙色分散性染料20~98重量%、及上述式[17]所表示之染料2~80重量%。更佳為,該橙色分散性染料為25~85重量%、該式[17]之染料為15~75重量%,再更佳為,該橙色分散性染料為30~70重量%、該式[17]之染料為70~30重量%。The orange-based second disperse dye composition of the present invention preferably contains 20 to 98% by weight of the orange disperse dye represented by the above formula [1] and 2 to 80 of the dye represented by the above formula [17]. weight%. More preferably, the orange disperse dye is 25 to 85% by weight, the dye of the formula [17] is 15 to 75% by weight, and even more preferably, the orange disperse dye is 30 to 70% by weight, the formula [ 17] The dye is 70 to 30% by weight.
本發明之黃色~橙色系之第1分散性染料組成物之中,配合用之橙色系分散性染料組成物(以下,稱為「第1配合用橙色系分散性染料組成物」),可與其他紅色系染料及藍色系染料配合,而使用於茶色、深藍色、黑色用分散性染料之製作。由上色染深性等之觀點考量,第1配合用橙色系分散性染料組成物,較佳為,含有該橙色分散性染料為65~98重量%、及選自上述式[2]所表示之染料、上述式[3]所表示之染料、上述式[4]所表示之染料、上述式[5]所表示之染料、及上述式[6]所表示之染料中之至少一種黃色系染料2~35重量%。更佳為,該橙色分散性染料為75~97重量%、該黃色系染料為3~25重量%,再更佳為,該橙色分散性染料為85~96重量%、該黃色系染料為4~15重量%。In the yellow-orange-based first disperse dye composition of the present invention, an orange-based disperse dye composition (hereinafter referred to as "the first compound orange disperse dye composition") can be used in combination with Other red dyes and blue dyes are used in combination with brown, dark blue, and black disperse dyes. The orange-based disperse dye composition for the first compounding is preferably 65 to 98% by weight, and is selected from the above formula [2], from the viewpoint of coloring and the like. The dye, the dye represented by the above formula [3], the dye represented by the above formula [4], the dye represented by the above formula [5], and at least one of the dyes represented by the above formula [6] 2~35 wt%. More preferably, the orange disperse dye is 75 to 97% by weight, the yellow dye is 3 to 25% by weight, and more preferably, the orange disperse dye is 85 to 96% by weight, and the yellow dye is 4 ~15% by weight.
又,本發明之橙色系之第2分散性染料組成物之中,其他之配合用之橙色系分散性染料組成物(以下,稱為「第2配合用橙色系分散性染料組成物」),較佳為,含有該橙色分散性染料20~80重量%、及上述式[17]所表示之染料20~80重量%。更佳為,該橙色分散性染料為25~75重量%、該式[17]之染料為75~25重量%,再更佳為,該橙色分散性染料為30~70重量%、該式[17]之染料為70~30重量%。Further, among the orange-based second disperse dye compositions of the present invention, the other orange-based disperse dye composition (hereinafter referred to as "the second compound-containing orange disperse dye composition") is used. It is preferable to contain 20 to 80% by weight of the orange disperse dye and 20 to 80% by weight of the dye represented by the above formula [17]. More preferably, the orange disperse dye is 25 to 75% by weight, the dye of the formula [17] is 75 to 25% by weight, and more preferably, the orange disperse dye is 30 to 70% by weight, the formula [ 17] The dye is 70 to 30% by weight.
又,該橙色系之第1分散性染料組成物之中,當做為噴墨印染用墨水之黑色使用時,較佳為,使用上述式[3]所表示之染料做為該黃色系染料之該第1配合用橙色系分散性染料組成物。Further, in the orange-based first disperse dye composition, when used as black for inkjet printing ink, it is preferred to use the dye represented by the above formula [3] as the yellow dye. The first compound is an orange-based disperse dye composition.
配合於該第1及第3分散性染料組成物之選自上述式[2]所表示之染料、上述式[3]所表示之染料、上述式[4]所表示之染料、上述式[5]所表示之染料、及上述式[6]所表示之染料中之至少一種黃色系染料中,式[4]所表示之染料及式[6]所表示之染料之具體例,可舉例如下述式[4-1]所表示之染料、下述式[4-2]所表示之染料、下述式[4-3]所表示之染料、下述式[6-1]所表示之染料、下述式[6-2]所表示之染料。The dye represented by the above formula [2], the dye represented by the above formula [3], the dye represented by the above formula [4], and the above formula [5] are blended in the first and third disperse dye compositions. In the dye represented by the dye and the dye represented by the formula [6], the dye represented by the formula [4] and the dye represented by the formula [6], for example, may be, for example, the following a dye represented by the formula [4-1], a dye represented by the following formula [4-2], a dye represented by the following formula [4-3], a dye represented by the following formula [6-1], A dye represented by the following formula [6-2].
本發明之第3分散性染料組成物,較佳為,含有該橙色分散性染料或該第1配合用橙色系分散性染料組成物5~50重量%、及選自上述式[7]所表示之染料、上述式[8]所表示之染料、上述式[9]所表示之染料、上述式[10]所表示之染料、及上述式[11]所表示之染料中之至少一種紅色系染料3~50重量%、以及選自上述式[12]所表示之染料、上述式[13]所表示之染料、上述式[14]所表示之染料、上述式[15]所表示之染料、及上述式[16]所表示之染料中之至少一種藍色系染料10~90重量%。藉由作成上述之混合比例,可製作高耐光性之茶色、深藍色、黑色用分散性染料組成物。又,欲製得灰色之染色物時,可藉由降低該黑色用分散性染料組成物之染色濃度來得到所欲之色相。再者,更佳為,該橙色分散性染料或該第1配合用橙色系分散性染料組成物為15~45重量%、該紅色系染料為5~40重量%、該藍色系染料為20~85重量%。The third disperse dye composition of the present invention preferably contains the orange disperse dye or the first disperse orange disperse dye composition in an amount of 5 to 50% by weight, and is selected from the above formula [7]. The dye, the dye represented by the above formula [8], the dye represented by the above formula [9], the dye represented by the above formula [10], and at least one red dye of the dye represented by the above formula [11] 3 to 50% by weight, and a dye represented by the above formula [12], a dye represented by the above formula [13], a dye represented by the above formula [14], a dye represented by the above formula [15], and At least one of the dyes represented by the above formula [16] is 10 to 90% by weight. By making the above mixing ratio, it is possible to produce a disperse dye composition for brown, dark blue, and black having high light resistance. Further, in order to obtain a gray dye, the desired hue can be obtained by lowering the dyeing concentration of the black disperse dye composition. Furthermore, it is more preferable that the orange disperse dye or the first disperse orange disperse dye composition is 15 to 45% by weight, the red dye is 5 to 40% by weight, and the blue dye is 20 ~85% by weight.
又,該第3及第4分散性染料組成物之中,當做為噴墨印染用墨水之黑色使用時,較佳為,使用上述式[8]所表示之染料做為該紅色系染料之該第3及第4分散性染料組成物。Further, among the third and fourth disperse dye compositions, when used as black for ink for inkjet printing, it is preferred to use the dye represented by the above formula [8] as the red dye. The third and fourth disperse dye compositions.
又,將疏水性纖維以浸染法或印染法進行染色時,較佳為,使用上述式[14]所表示之染料、上述式[15]所表示之染料、及上述式[16]所表示之染料做為藍色系染料之該第3及第4分散性染料組成物。做為噴墨印染用墨水之黑色使用時,較佳為,使用上述式[12]所表示之染料或式[13]所表示之染料做為該藍色系染料之該第3及第4分散性染料組成物。Further, when the hydrophobic fiber is dyed by a dip dyeing method or a printing method, it is preferred to use the dye represented by the above formula [14], the dye represented by the above formula [15], and the formula [16]. The dye is used as the third and fourth disperse dye compositions of the blue dye. In the case of using black ink for inkjet printing, it is preferred to use the dye represented by the above formula [12] or the dye represented by the formula [13] as the third and fourth dispersion of the blue dye. Sex dye composition.
於該第3及第4分散性染料組成物中所配合之上述式[7]所表示之染料、上述式[8]所表示之染料、上述式[9]所表示之染料、上述式[10]所表示之染料、及上述式[11]所表示之染料中該式[8][10]及[11]之染料的具體例,可舉例如下述式[8-1]所表示之染料、下述式[8-2]所表示之染料、下述式[8-3]所表示之染料、下述式[10-1]所表示之染料、下述式[10-2]所表示之染料、下述式[11-1]所表示之染料、下述式[11-2]所表示之染料。The dye represented by the above formula [7], the dye represented by the above formula [8], the dye represented by the above formula [9], and the above formula [10] are blended in the third and fourth disperse dye compositions. Specific examples of the dyes of the formula [8] [10] and [11] in the dye represented by the above formula [11], for example, the dye represented by the following formula [8-1], The dye represented by the following formula [8-2], the dye represented by the following formula [8-3], the dye represented by the following formula [10-1], and the following formula [10-2] The dye, the dye represented by the following formula [11-1], and the dye represented by the following formula [11-2].
於該第3及第4分散性染料組成物中所配合之上述式[12]所表示之染料、上述式[13]所表示之染料、上述式[14]所表示之染料、上述式[15]所表示之染料、及上述式[16]所表示之染料中,該式[13]所表示之染料、該式[15]所表示之染料及該式[16]所表示之染料的具體例,可舉例如下述式[13-1]所表示之染料、下述式[15-1]所表示之染料、下述式[15-2]所表示之染料、下述式[15-3]所表示之染料、下述式[16-1]所表示之染料、下述式[16-2]所表示之染料。The dye represented by the above formula [12], the dye represented by the above formula [13], the dye represented by the above formula [14], and the above formula [15] are blended in the third and fourth disperse dye compositions. The dye represented by the above formula [16], the dye represented by the formula [13], the dye represented by the formula [15], and the specific examples of the dye represented by the formula [16] For example, the dye represented by the following formula [13-1], the dye represented by the following formula [15-1], the dye represented by the following formula [15-2], and the following formula [15-3] The dye represented by the following formula [16-1], and the dye represented by the following formula [16-2].
對上述高耐光性之茶色、深藍色或黑色用分散性染料組成物,進行更具體的說明。茶色用分散性染料組成物,較佳為,含有該橙色分散性染料或該第1配合用橙色系分散性染料組成物20~50重量%、及選自上述式[7]所表示之染料、上述式[8]所表示之染料、上述式[9]所表示之染料、上述式[10]所表示之染料、及上述式[11]所表示之染料中之至少一種紅色系染料20~50重量%、以及選自上述式[12]所表示之染料、上述式[13]所表示之染料、上述式[14]所表示之染料、上述式[15]所表示之染料、及上述式[16]所表示之染料中之至少一種藍色系染料10~50重量%。更佳為,茶色用分散性染料組成物,含有該橙色分散性染料或該第1配合用橙色系分散性染料組成物25~45重量%、該紅色系染料25~40重量%及該藍色系染料20~40重量%。The above-mentioned highly light-resistant brown, dark blue or black disperse dye composition will be more specifically described. The disperse dye composition for brown color, preferably containing the orange disperse dye or the first disperse orange disperse dye composition in an amount of 20 to 50% by weight, and a dye selected from the above formula [7]. The dye represented by the above formula [8], the dye represented by the above formula [9], the dye represented by the above formula [10], and at least one of the dyes represented by the above formula [11], 20 to 50 And a dye represented by the above formula [12], a dye represented by the above formula [14], a dye represented by the above formula [15], and the above formula [ 16] at least one of the dyes represented by the blue dye is 10 to 50% by weight. More preferably, the disperse dye composition for brown color contains the orange disperse dye or the first disperse orange disperse dye composition in an amount of 25 to 45% by weight, the red dye 25 to 40% by weight, and the blue color. The dye is 20-40% by weight.
又,深藍色用分散性染料組成物,較佳為,含有該橙色分散性染料或該第1配合用橙色系分散性染料組成物5~20重量%、及選自上述式[7]所表示之染料、上述式[8]所表示之染料、上述式[9]所表示之染料、上述式[10]所表示之染料、及上述式[11]所表示之染料中之至少一種紅色系染料3~25重量%、以及選自上述式[12]所表示之染料、上述式[13]所表示之染料、上述式[14]所表示之染料、上述式[15]所表示之染料、及上述式[16]所表示之染料中之至少一種藍色系染料60~90重量%。更佳為,深藍色用分散性染料組成物,含有該橙色分散性染料或該第1配合用橙色系分散性染料組成物10~15重量%、該紅色系染料5~20重量%及該藍色系染料65~85重量%。Further, the dark blue disperse dye composition preferably contains the orange disperse dye or the first blend orange disperse dye composition in an amount of 5 to 20% by weight, and is selected from the above formula [7]. The dye, the dye represented by the above formula [8], the dye represented by the above formula [9], the dye represented by the above formula [10], and at least one red dye of the dye represented by the above formula [11] 3 to 25% by weight, and a dye represented by the above formula [12], a dye represented by the above formula [13], a dye represented by the above formula [14], a dye represented by the above formula [15], and At least one of the dyes represented by the above formula [16] is 60 to 90% by weight. More preferably, the dark blue disperse dye composition contains the orange disperse dye or the first blending orange disperse dye composition in an amount of 10 to 15% by weight, the red dye in an amount of 5 to 20% by weight, and the blue The color dye is 65 to 85% by weight.
又,黑色用分散性染料組成物,較佳為,含有該橙色分散性染料或該第1配合用橙色系分散性染料組成物20~45重量%、及選自上述式[7]所表示之染料、上述式[8]所表示之染料、上述式[9]所表示之染料、上述式[10]所表示之染料、及上述式[11]所表示之染料中之至少一種紅色系染料5~25重量%、以及選自上述式[12]所表示之染料、上述式[13]所表示之染料、上述式[14]所表示之染料、上述式[15]所表示之染料、及上述式[16]所表示之染料中之至少一種藍色系染料45~70重量%。更佳為,黑色用分散性染料組成物,含有該橙色分散性染料或該第1配合用橙色系分散性染料組成物25~40重量%、該紅色系染料5~20重量%及該藍色系染料50~65重量%。Further, the disperse dye composition for black preferably contains the orange disperse dye or the first disperse orange disperse dye composition in an amount of 20 to 45% by weight, and is selected from the group consisting of the above formula [7]. The dye, the dye represented by the above formula [8], the dye represented by the above formula [9], the dye represented by the above formula [10], and at least one red dye 5 of the dye represented by the above formula [11] ~25% by weight, and a dye represented by the above formula [12], a dye represented by the above formula [13], a dye represented by the above formula [14], a dye represented by the above formula [15], and the above At least one of the dyes represented by the formula [16] is 45 to 70% by weight. More preferably, the disperse dye composition for black contains the orange disperse dye or the first disperse orange disperse dye composition in an amount of 25 to 40% by weight, the red dye in an amount of 5 to 20% by weight, and the blue color. The dye is 50~65% by weight.
又,本發明之第4分散性染料組成物,其特徵在於,含有第2配合用橙色系分散性染料組成物、及選自上述式[7]所表示之染料、上述式[8]所表示之染料、上述式[9]所表示之染料、上述式[10]所表示之染料、及上述式[11]所表示之染料中之至少一種紅色系染料、以及選自上述式[12]所表示之染料、上述式[13]所表示之染料、上述式[14]所表示之染料、上述式[15]所表示之染料、及上述式[16]所表示之染料中之至少一種藍色系染料。該第4分散性染料組成物,較佳為,含有第2配合用橙色系分散性染料組成物5~50重量%、該紅色系染料3~50重量%、及該藍色系染料10~90重量%。Furthermore, the fourth disperse dye composition of the present invention is characterized in that it contains a second dispersing orange-based disperse dye composition and a dye selected from the above formula [7] and represented by the above formula [8]. a dye, a dye represented by the above formula [9], a dye represented by the above formula [10], and at least one red dye of the dye represented by the above formula [11], and a dye selected from the above formula [12] The dye represented by the above formula [13], the dye represented by the above formula [14], the dye represented by the above formula [15], and at least one of the dyes represented by the above formula [16] Is a dye. The fourth disperse dye composition preferably contains 5 to 50% by weight of the second orange-based disperse dye composition, 3 to 50% by weight of the red dye, and 10 to 90 of the blue dye. weight%.
再者,該第1至第4分散性染料組成物,於不使耐光堅牢度降低之範圍內,可添加色相調整用之其他分散性染料。Further, in the first to fourth disperse dye compositions, other disperse dyes for adjusting the hue can be added within a range in which the light fastness is not lowered.
針對本發明之該橙色分散性染料及染料之調合物的調製方法進行說明。上述式[1]所表示之染料、上述式[2]所表示之染料、上述式[3]所表示之染料、上述式[4]所表示之染料、上述式[5]所表示之染料、上述式[6]所表示之染料、上述式[7]所表示之染料、上述式[8]所表示之染料、上述式[9]所表示之染料、上述式[10]所表示之染料、上述式[11]所表示之染料、上述式[12]所表示之染料、上述式[13]所表示之染料、上述式[14]所表示之染料、上述式[15]所表示之染料、上述式[16]所表示之染料及上述式[17]所表示之染料,可依一般方法,例如於上述染料之濕餅中添加做為分散劑之萘磺酸之甲醛縮合物、木質磺酸系等陰離子界面活性劑、與水,以砂磨機等微粒子化而製得上述染料之分散液。該微粒子之平均粒徑,染色用以約0.2~1.0μm為佳、噴墨用以0.5μm以下為佳。該橙色系分散性染料及染料之調合物,可以所得之分散液、或將其乾燥所得之粉末型態使用。A method of preparing the blend of the orange disperse dye and the dye of the present invention will be described. The dye represented by the above formula [1], the dye represented by the above formula [2], the dye represented by the above formula [3], the dye represented by the above formula [4], the dye represented by the above formula [5], The dye represented by the above formula [6], the dye represented by the above formula [7], the dye represented by the above formula [8], the dye represented by the above formula [9], the dye represented by the above formula [10], The dye represented by the above formula [11], the dye represented by the above formula [12], the dye represented by the above formula [13], the dye represented by the above formula [14], the dye represented by the above formula [15], The dye represented by the above formula [16] and the dye represented by the above formula [17] can be added to a wet cake of the above dye by a general method, for example, a formaldehyde condensate of naphthalenesulfonic acid as a dispersing agent, and lignosulfonic acid. An anionic surfactant such as an anion surfactant, and water, which are micronized by a sand mill or the like to obtain a dispersion of the above dye. The average particle diameter of the fine particles is preferably about 0.2 to 1.0 μm for dyeing and 0.5 μm or less for inkjet. The orange-based disperse dye and the blend of the dyes can be used in the resulting dispersion or in a powder form obtained by drying the obtained dispersion.
針對本發明之該第1至第4分散性染料組成物、以及第1及第2配合用分散性染料組成物之調製方法進行說明。該第1至第4分散性染料組成物以及第1及第2配合用分散性染料組成物,可藉由配合分散液或將其乾燥所得之粉末型態之該橙色分散性染料及染料之調合物來製得。The first to fourth disperse dye compositions of the present invention and the preparation method of the first and second disperse dye compositions for blending will be described. The first to fourth disperse dye compositions and the first and second disperse dye compositions for blending can be blended with the disperse or the powder form of the orange disperse dye and dye obtained by drying the dispersion. Made of things.
針對使用該橙色分散性染料、該第1至第4分散性染料組成物、以及第1及第2配合用分散性染料組成物對疏水性纖維材料進行染色之方法進行說明。首先,分別使該橙色分散性染料及該染料組成物之調合物分散於水性介質中,並視需要添加pH調整劑、分散均染劑等以準備染色浴。於該染色浴,浸漬疏水性纖維材料。該浸漬,例如當為聚酯纖維時,係於加壓下、於例如105℃以上、較佳為110~140℃之溫度範圍進行。又,該染色浴,亦可再含有鄰苯基苯酚、甲基萘、三氯苯等載體,於含上述載體之染色浴中所進行之浸漬,可以較低溫、例如100~110℃之溫度範圍進行。又,亦可將於水性介質中分別分散有該橙色分散性染料、該第1至第4分散性染料組成物、以及第1及第2配合用分散性染料組成物之該染料分散液,浸染於布,以100℃以上溫度之蒸烘方式或施以乾熱處理之所謂熱熔膠方式來進行染色。又,該橙色分散性染料及該分散性染料組成物,亦可與天然糊劑(例如,刺槐豆膠、關華豆膠、雪藻脂(snow algin)、酪蛋白等)、加工糊劑(例如,羧基甲基纖維素等纖維素衍生物、加工刺槐豆膠等)、合成糊劑(例如,聚乙烯醇、聚乙烯乙酸等)、抗還原劑、pH調整劑、濃染劑等一起調製成印染糊劑,使用該印染糊劑印染於布後,以進行蒸烘或熱溶處理之印染法來染色。再者,亦可使用紫外線吸收劑以製得耐光性優異之染色物。該紫外線吸收劑之使用量,並無特別限制,對於被染物,較佳為0.5~5重量%(對布100g為0.5~5g之比例)、最佳為1~2重量%。A method of dyeing a hydrophobic fibrous material using the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions for blending will be described. First, the orange disperse dye and the blend of the dye composition are dispersed in an aqueous medium, and a pH adjuster, a disperse leveling agent, or the like is added as needed to prepare a dye bath. The hydrophobic fiber material is impregnated in the dye bath. The impregnation, for example, in the case of a polyester fiber, is carried out under pressure, for example, at a temperature of, for example, 105 ° C or higher, preferably 110 to 140 ° C. Further, the dyeing bath may further contain a carrier such as o-phenylphenol, methylnaphthalene or trichlorobenzene, and may be impregnated in a dye bath containing the carrier at a lower temperature, for example, a temperature range of 100 to 110 °C. get on. Further, the dye dispersion liquid of the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions may be dispersed in an aqueous medium, and may be impregnated. In the cloth, the dyeing is carried out by a steam drying method at a temperature of 100 ° C or higher or a so-called hot melt method using a dry heat treatment. Further, the orange disperse dye and the disperse dye composition may be combined with a natural paste (for example, locust bean gum, Guanhua bean gum, snow algin, casein, etc.), a processing paste ( For example, a cellulose derivative such as carboxymethylcellulose or a processed locust bean gum, a synthetic paste (for example, polyvinyl alcohol, polyvinyl acetate, etc.), an anti-reducing agent, a pH adjuster, a dyeing agent, and the like are prepared together. The paste is printed on the cloth using the printing paste, and is dyed by a printing method of steaming or hot-dissolving. Further, an ultraviolet absorber can also be used to obtain a dyed product excellent in light resistance. The amount of the ultraviolet absorber to be used is not particularly limited, and is preferably 0.5 to 5% by weight (ratio of 0.5 to 5 g to 100 g of the cloth), and preferably 1 to 2% by weight, based on the dye.
本發明之以該橙色分散性染料、該第1至第4分散性染料組成物、以及第1及第2配合用分散性染料組成物染色所得之疏水性纖維材料之具體例,只要為一般分散性染料組成物所染色者即可,並無特別限制,可舉例如聚對苯二甲酸乙二醇酯、對苯二甲酸與1,4-雙(羥甲基)環己烷之縮聚物等之聚酯纖維、三乙酸酯纖維、二乙酸酯纖維及該等之混紡品、或該等與木棉、絹、羊毛等天然纖維或尼龍等合成纖維與上述纖維之混紡品、混織物等。Specific examples of the hydrophobic fibrous material obtained by dyeing the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions of the present invention are generally dispersed. The dye composition is not particularly limited, and examples thereof include polyethylene terephthalate, terephthalic acid, and polycondensate of 1,4-bis(hydroxymethyl)cyclohexane. Polyester fiber, triacetate fiber, diacetate fiber and blended products thereof, or blended with synthetic fibers such as kapok, ray, wool, or natural fibers such as nylon or the like, mixed fabrics, etc. .
又,該疏水性纖維材料,可舉例如細丹尼(finedenier)聚酯纖維。細丹尼聚酯纖維,係做為汽車內裝用(特別是座椅片的材質)使用,由於其觸感受消費者接受故市場正擴大中。其係聚酯纖維中,纖度極細化者[通常為纖度1.0d(denier,丹尼)以下之纖維,以纖度為0.01~0.4d(丹尼)更佳],亦稱為超細纖維(microfiber)或新合纖。該等極細纖維,即使與粗纖維為相同染料吸盡率(染色(build up)率),由人的眼睛觀看較為淡色,故適於使用本發明之分散性染料來展現濃色調。再者,新合纖之中亦有結晶配向性高之聚酯,而該等聚酯難以染色,故適於使用本發明之分散性染料來展現濃色調。Further, the hydrophobic fibrous material may, for example, be a fine denier polyester fiber. The fine denier polyester fiber is used as a car interior (especially the material of the seat piece), and the market is expanding due to its acceptance of the consumer. Among the polyester fibers, the fineness is extremely fine [usually a fiber having a fineness of 1.0 d (denier) or less, and a fineness of 0.01 to 0.4 d (denier) is better], also known as microfiber (microfiber). ) or new synthetic fiber. These ultrafine fibers are suitable for use in the use of the disperse dye of the present invention to exhibit a rich color tone even if the same dye exhaustion rate (build up rate) is the same as that of the crude fiber and is lightly colored by the human eye. Further, among the new synthetic fibers, there are also polyesters having high crystal alignment, and these polyesters are difficult to dye, so that it is suitable to use the disperse dye of the present invention to exhibit a rich color tone.
本發明之噴墨印染用墨水,係含有該橙色分散性染料、該第1至第4分散性染料組成物、以及第1及第2配合用分散性染料組成物。The ink for inkjet printing of the present invention contains the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions for mixing.
本發明之噴墨印染用墨水,較佳為,於平均粒徑微粒子化為0.5μm以下之該橙色分散性染料或該分散性染料組成物之分散液,視需要添加水、水溶性有機溶劑、分散劑等各種添加劑來製造。該平均粒徑,由防止噴嘴阻塞的觀點考量,以0.05~0.2μm較佳。The ink for inkjet printing of the present invention is preferably a dispersion of the orange disperse dye or the disperse dye composition having an average particle diameter of 0.5 μm or less, optionally adding water or a water-soluble organic solvent. It is produced by various additives such as a dispersant. The average particle diameter is preferably from 0.05 to 0.2 μm from the viewpoint of preventing nozzle clogging.
該染料之含量,一般而言,由於保持分散安定性、且可得必要之印字濃度,對墨水總重量,以0.5~15重量%為佳。更佳為,該染料之含量為1~12重量%。The content of the dye is generally 0.5 to 15% by weight based on the total weight of the ink, since the dispersion stability is maintained and the necessary printing density is obtained. More preferably, the dye is present in an amount of from 1 to 12% by weight.
本發明所使用之水溶性有機溶劑,可舉例如乙二醇、二乙二醇、丙二醇、丁二醇、三乙二醇、四乙二醇、聚乙二醇、聚丙二醇、硫二乙二醇、甘油、二甘油等多元醇類、乙二醇單甲醚、二乙二醇單甲醚、二乙二醇單***、二乙二醇單丁醚、丙二醇單甲醚等二醇醚類、異丙醇、甲醇、乙醇、苄醇等醇類、N-甲基-2-吡咯烷酮、三乙醇胺等鹼性溶劑。The water-soluble organic solvent used in the present invention may, for example, be ethylene glycol, diethylene glycol, propylene glycol, butylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, polypropylene glycol or thiodiethylene. Polyols such as alcohol, glycerin and diglycerin, glycol ethers such as ethylene glycol monomethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, diethylene glycol monobutyl ether, and propylene glycol monomethyl ether An alcohol such as isopropanol, methanol, ethanol or benzyl alcohol, or an alkaline solvent such as N-methyl-2-pyrrolidone or triethanolamine.
上述水溶性有機溶劑之中,以甘油、二乙二醇、聚乙二醇300、400、丙二醇為佳。特別是,甘油以做為保濕劑為佳。Among the above water-soluble organic solvents, glycerin, diethylene glycol, polyethylene glycol 300, 400, and propylene glycol are preferred. In particular, glycerin is preferred as a moisturizer.
該等水溶性有機溶劑,可單獨使用、亦可混合2種以上使用。These water-soluble organic solvents may be used singly or in combination of two or more.
該等水溶性有機溶劑之含量,由墨水之黏度調整、防止保濕效果所致之阻塞的觀點考量,對墨水總重量,以5~50重量%為佳。水溶性有機溶劑之含量,對墨水總重量,以10~45重量%為更佳、15~40重量%為特佳。The content of the water-soluble organic solvent is preferably from 5 to 50% by weight based on the total viscosity of the ink, from the viewpoint of adjusting the viscosity of the ink and preventing the clogging caused by the moisturizing effect. The content of the water-soluble organic solvent is preferably from 10 to 45% by weight, more preferably from 15 to 40% by weight, based on the total weight of the ink.
本發明所使用之分散劑,係將該橙色分散性染料、該第1至第4分散性染料組成物、以及第1及第2配合用分散性染料組成物分散於水性介質中者,並無特別限定,例如,陰離子性界面活性劑、非離子性界面活性劑,而以陰離子性界面活性劑為佳。The dispersing agent used in the present invention is one in which the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions are dispersed in an aqueous medium. Particularly, for example, an anionic surfactant or a nonionic surfactant is preferred, and an anionic surfactant is preferred.
該陰離子性界面活性劑,可舉例如萘磺酸鹽之甲醛縮合物、木質磺酸鹽類、特殊芳香族磺酸鹽之甲醛縮合物、雜酚油磺酸鹽之甲醛縮合物、聚氧乙烯烷基醚硫酸鹽等。The anionic surfactant may, for example, be a formaldehyde condensate of a naphthalenesulfonate, a lignosulfonate, a formaldehyde condensate of a special aromatic sulfonate, a formaldehyde condensate of a creosote sulfonate, or a polyoxyethylene. Alkyl ether sulfates and the like.
該非離子性界面活性劑,可舉例如聚氧化乙烯去水山梨糖醇脂肪酸酯、聚氧化乙烯烷基醚、聚氧化乙烯烷基苯醚、聚氧化乙烯衍生物、聚氧化乙烯.氧化丙烯嵌段聚合物等。The nonionic surfactant may, for example, be a polyoxyethylene sorbitan fatty acid ester, a polyoxyethylene alkyl ether, a polyoxyethylene alkyl phenyl ether, a polyoxyethylene derivative, a polyethylene oxide or a propylene oxide. Segment polymer and the like.
該等分散劑之含量,由良好保持該橙色分散性染料、該第1至第4分散性染料組成物、以及第1及第2配合用分散性染料組成物之分散安定性之目的,對墨水總重量,以0.5~20重量%為佳。該分散劑之含量,更佳為0.5~10重量%、特佳為0.5~5重量%。The content of the dispersant is good for the purpose of maintaining the dispersion stability of the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions. The total weight is preferably 0.5 to 20% by weight. The content of the dispersant is more preferably 0.5 to 10% by weight, particularly preferably 0.5 to 5% by weight.
藉由再含有下述式(I)所示之化合物(式中,R表示碳數25~50之烷基,n表示10~100),可得再分散性佳之噴墨紀錄用墨水組成物。由連續噴出安定性及長時間放置後之噴出性、長期保存安定的觀點考量,下述式(I)中,R,較佳為碳數30~50之烷基、更佳為碳數30~35之烷基。下述式(I)中,n,較佳為20~100、更佳為30~100。又,該烷基可為直鏈或具支鏈,而以直鏈狀烷基為佳。By further containing a compound represented by the following formula (I) (wherein R represents an alkyl group having a carbon number of 25 to 50 and n represents 10 to 100), an ink composition for ink jet recording which is excellent in redispersibility can be obtained. From the viewpoint of continuous discharge stability and long-term storage stability after long-term storage, R in the following formula (I) is preferably an alkyl group having 30 to 50 carbon atoms, more preferably 30 carbon atoms. 35 alkyl. In the following formula (I), n is preferably from 20 to 100, more preferably from 30 to 100. Further, the alkyl group may be linear or branched, and a linear alkyl group is preferred.
R-O-(CH2 CH2 O)n -H (I)R-O-(CH 2 CH 2 O) n -H (I)
該化合物(I)之HLB,由於水的溶解性觀點考量,例如為10以上。該HLB,較佳為14~18。The HLB of the compound (I) is, for example, 10 or more in view of water solubility. The HLB is preferably 14-18.
上述式(I)之化合物,對墨水總量,較佳為使用0.1~8重量%、更佳為0.1~6重量%、再更佳為0.2~4重量%。藉由將該式(I)之化合物以0.1~8重量%的範圍使用,即使添加量過高墨水的黏度亦無過高的問題,且亦可發揮提昇再分散性的效果,故較佳。The compound of the above formula (I) is preferably used in an amount of 0.1 to 8% by weight, more preferably 0.1 to 6% by weight, still more preferably 0.2 to 4% by weight based on the total amount of the ink. By using the compound of the formula (I) in an amount of 0.1 to 8% by weight, even if the amount of the ink is too high, the viscosity of the ink is not excessively high, and the effect of improving the redispersibility can be exhibited, which is preferable.
該式(I)之化合物之例,可舉例如美國貝德羅萊特公司製之「攸尼德克斯450」(R為碳數30之直鏈烷基,n為約10,HLB=10)、「攸尼德克斯480」(R為碳數30之直鏈烷基,n為約40,HLB=16)、「攸尼德克斯490」(R為碳數30之直鏈烷基,n為約94,HLB=18)、「攸尼德克斯550」(R為碳數40之直鏈烷基,n為約12,HLB=10)、「攸尼德克斯750」(R為碳數50之直鏈烷基,n為約16,HLB=10)等。其中,做為該式(I)之化合物,以「攸尼德克斯480」及「攸尼德克斯490」為佳。Examples of the compound of the formula (I) include "Monidex 450" manufactured by Bedrolet, Inc. (R is a linear alkyl group having a carbon number of 30, n is about 10, and HLB = 10). "攸尼德克斯480" (R is a linear alkyl group having a carbon number of 30, n is about 40, HLB = 16), and "Monidex 490" (R is a linear alkyl group having a carbon number of 30) , n is about 94, HLB = 18), "Monidus 550" (R is a linear alkyl group with a carbon number of 40, n is about 12, HLB = 10), "Unines 750" ( R is a linear alkyl group having a carbon number of 50, n is about 16, HLB = 10) or the like. Among them, as the compound of the formula (I), "攸尼德克斯480" and "攸尼德克斯490" are preferred.
又,當添加該式(I)之化合物時,由作業性的觀點,以5~15重量%左右之式(I)之化合物的水溶液型態添加為佳。Further, when the compound of the formula (I) is added, it is preferably added in an aqueous solution form of the compound of the formula (I) in an amount of from 5 to 15% by weight from the viewpoint of workability.
於本發明之墨水,於不妨礙達成本發明之目的的範圍內,可視需要添加其他各種添加劑。其他各種添加劑,例如,有表面調整劑、增溶劑、pH調整劑、黏度調整劑、防腐劑、防黴劑、光安定劑、螯合劑、消泡劑等。In the ink of the present invention, various other additives may be added as needed within the range not inhibiting the object of the present invention. Other various additives, for example, surface conditioning agents, solubilizers, pH adjusters, viscosity modifiers, preservatives, mildew inhibitors, light stabilizers, chelating agents, antifoaming agents, and the like.
上述添加劑之中,有表面調整劑,可舉例如氟系界面活性劑、聚醚變性聚二甲基矽氧烷、丙烯酸系聚合物等,特別以聚醚變性聚二甲基矽氧烷或丙烯酸系聚合物為佳。該等表面調整劑,係對於調整墨水之表面張力、使墨水容易濕潤墨水通路系材料有效。該表面調整劑,對於墨水總重量,例如係以0.05~1重量%(較佳為0.1~0.5重量%)的範圍使用。若將該表面調整劑以對墨水總重量之0.05重量%以上使用,則表面調整效果增高,而若使用1重量%以下,則可得一定高之表面調整效果。Among the above additives, there may be a surface conditioning agent, and examples thereof include a fluorine-based surfactant, a polyether-denatured polydimethylsiloxane, an acrylic polymer, and the like, particularly a polyether-denatured polydimethylsiloxane or acrylic acid. The polymer is preferred. These surface conditioners are effective for adjusting the surface tension of the ink and making the ink easy to wet the ink passage material. The surface conditioning agent is used in a range of, for example, 0.05 to 1% by weight (preferably 0.1 to 0.5% by weight) based on the total weight of the ink. When the surface conditioning agent is used in an amount of 0.05% by weight or more based on the total weight of the ink, the surface conditioning effect is increased, and when 1% by weight or less is used, a surface conditioning effect of a certain height can be obtained.
本發明之噴墨記錄用墨水的調製方法,並無特別限制,較佳為,以下述之方法調製。亦即,首先,(a)將該橙色分散性染料、該第1至第4分散性染料組成物、以及第1及第2配合用分散性染料組成物所使用之各染料、分散劑、水、及視需要之水溶性有機溶劑或上述添加劑混合、攪拌,調製成預備分散液。其次,(b)將該預備分散液以砂磨機等濕式介質磨機分散,得上述各染料之分散液。(c)調製僅有該橙色分散性染料之墨水時,可於該分散液中,添加水、水溶性有機溶劑、視需要之上述添加劑以調整濃度後,以濾紙過濾後使用。又,調製該第1至第4分散性染料組成物以及第1及第2配合用分散性染料組成物之墨水時,可將配合用之各分散劑混合既定量,於該分散液中,添加水、水溶性有機溶劑、視需要之上述添加劑以調整濃度後,以濾紙過濾後使用。The method for preparing the ink for inkjet recording of the present invention is not particularly limited, and it is preferably prepared by the following method. In other words, (a) the dye, dispersant, and water used in the orange disperse dye, the first to fourth disperse dye compositions, and the first and second disperse dye compositions for mixing. And, if necessary, a water-soluble organic solvent or the above-mentioned additives are mixed and stirred to prepare a preliminary dispersion. Next, (b) the preliminary dispersion liquid is dispersed in a wet medium mill such as a sand mill to obtain a dispersion liquid of each of the above dyes. (c) When an ink having only the orange disperse dye is prepared, water, a water-soluble organic solvent, and optionally the above additives may be added to the dispersion to adjust the concentration, and then filtered and filtered using a filter paper. Further, when the inks of the first to fourth disperse dye compositions and the first and second dispersible dye compositions are prepared, the dispersants for blending can be mixed and quantified, and added to the dispersion. Water, a water-soluble organic solvent, and the above-mentioned additives as needed are adjusted to a concentration, and then filtered by a filter paper and used.
上述製程(a)及(b)中,當調製該第1至第4分散性染料組成物以及第1及第2配合用分散性染料組成物之墨水時,可將配合用各染料混合後,與分散劑一同分散得分散液,於該第1至第4分散性染料組成物以及第1及第2配合用分散性染料組成物之分散液,添加水、水溶性有機溶劑、視需要之上述添加劑以調整濃度。In the above processes (a) and (b), when the inks of the first to fourth disperse dye compositions and the first and second disperse dye compositions are prepared, the dyes for blending may be mixed. The dispersing liquid is dispersed together with the dispersing agent, and water, a water-soluble organic solvent, and the like are added to the dispersion of the first to fourth disperse dye compositions and the first and second dispersing dye compositions. Additives to adjust the concentration.
以上述方法所得之分散性染料的平均粒徑,較佳為0.5μm以下、更佳為0.05~0.2μm。The average particle diameter of the disperse dye obtained by the above method is preferably 0.5 μm or less, more preferably 0.05 to 0.2 μm.
以上,例示溶劑、色材、分散劑、其他成分,但本發明並不限於該例。The solvent, the color material, the dispersant, and other components are exemplified above, but the present invention is not limited to this example.
又,於噴墨印染用墨水,於黑墨水之配合所使用之染料,於上述式[1]所表示之染料、上述式[2]所表示之染料、上述式[3]所表示之染料、上述式[4]所表示之染料、上述式[5]所表示之染料、上述式[6]所表示之染料、上述式[7]所表示之染料、上述式[8]所表示之染料、上述式[9]所表示之染料、上述式[10]所表示之染料、上述式[11]所表示之染料、上述式[12]所表示之染料、上述式[13]所表示之染料、上述式[14]所表示之染料、上述式[15]所表示之染料、上述式[16]所表示之染料及上述式[17]所表示之染料之中,特佳為,上述式[1]所表示之橙色分散性染料、以上述式[3]所表示之染料做為黃色系染料、以上述式[8]所表示之染料做為紅色系染料、以上述式[12]所表示之染料及上述式[13]所表示之染料做為藍色系染料。In addition, the dye used in the inkjet printing ink, the dye represented by the above formula [1], the dye represented by the above formula [2], the dye represented by the above formula [3], The dye represented by the above formula [4], the dye represented by the above formula [5], the dye represented by the above formula [6], the dye represented by the above formula [7], the dye represented by the above formula [8], The dye represented by the above formula [9], the dye represented by the above formula [10], the dye represented by the above formula [11], the dye represented by the above formula [12], the dye represented by the above formula [13], The dye represented by the above formula [14], the dye represented by the above formula [15], the dye represented by the above formula [16], and the dye represented by the above formula [17] are particularly preferably the above formula [1]. The orange disperse dye represented by the above formula [3] is a yellow dye, and the dye represented by the above formula [8] is a red dye, and is represented by the above formula [12]. The dye and the dye represented by the above formula [13] are used as a blue dye.
又,以噴墨印染用墨水之印染,例如,可如以下方式進行。首先,將該噴墨印染用墨水安裝於壓電方式之噴墨印表機,噴出至施以防滲等前處理之聚酯布上,可形成所欲之影像。再者,將該布,例如以150~220℃之溫度進行加熱處理,而將分散性染料染色於聚酯纖維。之後,將未固著之分散性染料、分散劑等添加劑及前處理劑等以還原洗淨或水洗除去,藉由乾燥得上述影像之染色物。Further, printing with ink for inkjet printing can be carried out, for example, in the following manner. First, the ink for inkjet printing is attached to a piezoelectric inkjet printer, and is ejected onto a polyester cloth subjected to pretreatment such as anti-seepage to form a desired image. Further, the cloth is heat-treated at a temperature of, for example, 150 to 220 ° C to dye the disperse dye to the polyester fiber. Thereafter, an additive such as an unfixed disperse dye or a dispersant, a pretreatment agent, and the like are removed by reduction washing or water washing, and dried to obtain a dyed product of the above image.
以下,舉實施例以更具體說明本發明,但本發明之樣態並不限於該等。又,於下述實施例,「份」除特別說明以外係指「重量份」,又,「%」除特別說明以外係指「重量%」。Hereinafter, the present invention will be described more specifically by way of examples, but the aspects of the invention are not limited thereto. In addition, in the following examples, "parts" means "parts by weight" unless otherwise specified, and "%" means "% by weight" unless otherwise specified.
將N-氰乙基-N-羥基乙苯胺(18.7份)與β-甲基吡啶(10.9份)之混合物升溫至50℃。之後,將氯化苯甲醯(16.8份)於60~70℃以3小時滴入該混合物後,於同溫度下保持1小時,藉此製得N-氰乙基-N-苯甲醯氧乙苯胺。於該混合物加入磺胺酸(2份),並添加乙酸120份使其溶解,加冰以將該混合物調整為5~10℃而製得偶合劑溶液。A mixture of N-cyanoethyl-N-hydroxyethylaniline (18.7 parts) and β-methylpyridine (10.9 parts) was heated to 50 °C. Thereafter, benzamidine chloride (16.8 parts) was added dropwise to the mixture at 60 to 70 ° C for 3 hours, and then kept at the same temperature for 1 hour, thereby preparing N-cyanoethyl-N-benzonitrile. Ethyl aniline. Sulfamic acid (2 parts) was added to the mixture, and 120 parts of acetic acid was added thereto to dissolve, and ice was added to adjust the mixture to 5 to 10 ° C to prepare a coupling agent solution.
於冷卻至5℃之濃硫酸(50份)及43%亞硝基硫酸(29.2份)之混合物,以5~10℃之範圍緩緩添加2-胺基-3-氯-5-硝基-1-三氟甲苯(24份)。將該混合物以5~10℃保持4小時,以製得重氮化合物。A mixture of concentrated sulfuric acid (50 parts) and 43% nitrosylsulfuric acid (29.2 parts) cooled to 5 ° C, slowly added 2-amino-3-chloro-5-nitro group in the range of 5-10 ° C 1-Trifluorotoluene (24 parts). The mixture was kept at 5 to 10 ° C for 4 hours to obtain a diazo compound.
將該重氮化合物溶液,於適當添加冰以將溫度保持於5~10℃之下,以3小時滴入上述偶合劑溶液中,進行偶合反應。The diazonium compound solution was added to ice under appropriate conditions to maintain the temperature at 5 to 10 ° C, and the mixture was dropped into the above coupling agent solution over 3 hours to carry out a coupling reaction.
於之後之1小時之間,將反應混合物保持於5~10℃之後,以1000份之水清洗。將所得之混合物以48%氫氧化鈉水溶液調整為pH=4後,升溫至70℃。以同溫度攪拌1小時後,由上述混合物過濾取得生成物,將該生成物水洗、乾燥而製得下述式[1-1]所表示之單偶氮化合物54.3份。所製得之下述式[1-1]所表示之單偶氮化合物,於丙酮溶液中之最大吸收波長(λm a x )為423nm。The reaction mixture was maintained at 5 to 10 ° C between 1 hour thereafter and washed with 1000 parts of water. The obtained mixture was adjusted to pH = 4 with a 48% aqueous sodium hydroxide solution, and then warmed to 70 °C. After stirring for 1 hour at the same temperature, the product was obtained by filtration from the mixture, and the product was washed with water and dried to give 54.3 parts of the monoazo compound represented by the following formula [1-1]. The monoazo compound represented by the following formula [1-1] had a maximum absorption wavelength (λ m a x ) in an acetone solution of 423 nm.
除使用2-胺基-3-溴-5-硝基-1-三氟甲苯取代2-胺基-3-氯-5-硝基-1-三氟甲苯、及使用N-氰乙基-N-氰乙基氧乙苯胺取代N-氰乙基-N-苯甲醯氧乙苯胺以外,與實施例1以相同方式製得下述式[1-2]所表示之染料。又,N-氰乙基-N-氰乙基氧乙苯胺,係如以下方式製造。將N-氰乙基-N-羥基乙苯胺(18.7份)與丙烯腈(14.9份)之混合物升溫至80~90℃,於同溫度下保持2小時以製得N-氰乙基-N-氰乙基氧乙苯胺。In addition to 2-amino-3-bromo-5-nitro-1-trifluorotoluene substituted 2-amino-3-chloro-5-nitro-1-trifluorotoluene, and using N-cyanoethyl- A dye represented by the following formula [1-2] was obtained in the same manner as in Example 1 except that N-cyanoethyl oxyethylanilide was substituted for N-cyanoethyl-N-benzimidoxime. Further, N-cyanoethyl-N-cyanoethyl oxyethylaniline was produced in the following manner. A mixture of N-cyanoethyl-N-hydroxyethylaniline (18.7 parts) and acrylonitrile (14.9 parts) was heated to 80-90 ° C and kept at the same temperature for 2 hours to obtain N-cyanoethyl-N- Cyanoethyl oxyethyl aniline.
所製得之下述式[1-2]所表示之單偶氮化合物,於丙酮溶液中之最大吸收波長(λm a x )為429nm。The monoazo compound represented by the following formula [1-2] had a maximum absorption wavelength (λ m a x ) in an acetone solution of 429 nm.
除使用2-胺基-3-溴-5-硝基-1-三氟甲苯取代2-胺基-3-氯-5-硝基-1-三氟甲苯、及使用N-氰乙基-N-丁基氧乙苯胺取代N-氰乙基-N-苯甲醯氧乙苯胺以外,與實施例1以相同方式製得下述式[1-3]所表示之染料。又,N-氰乙基-N-丁基氧乙苯胺,係如以下方式製造。將N-氰乙基苯胺(14.6份)、氫氧化鎂(3.6份)與水(18.4份)的混合物升溫至70℃。之後,於該混合物中,於70~85℃以3小時滴入對甲苯磺酸正丁基賽路蘇醚(33.7份)後,以90~95℃保持10小時以製得N-氰乙基-N-丁基氧乙苯胺。In addition to 2-amino-3-bromo-5-nitro-1-trifluorotoluene substituted 2-amino-3-chloro-5-nitro-1-trifluorotoluene, and using N-cyanoethyl- A dye represented by the following formula [1-3] was obtained in the same manner as in Example 1 except that N-cyanoethylaniline was substituted for N-cyanoethyl-N-benzimidoxime. Further, N-cyanoethyl-N-butyloxyethylaniline was produced in the following manner. A mixture of N-cyanoethylaniline (14.6 parts), magnesium hydroxide (3.6 parts) and water (18.4 parts) was heated to 70 °C. Thereafter, n-cyanoethyl p-toluenesulfonate (33.7 parts) was added dropwise to the mixture at 70 to 85 ° C for 3 hours, and then kept at 90 to 95 ° C for 10 hours to obtain N-cyanoethyl group. -N-butyl oxyethyl aniline.
所製得之下述式[1-3]所表示之單偶氮化合物,於丙酮溶液中之最大吸收波長(λm a x )為432nm。The monoazo compound represented by the following formula [1-3] had a maximum absorption wavelength (λ m a x ) in an acetone solution of 432 nm.
將上述式[1-1]所表示之染料30份,於萘磺酸之甲醛縮合物35份與水85份中,以砂磨機微粒子化,接著加入木質磺酸30份後,將所得之混合物噴霧乾燥,製得該式[1-1]所表示之染料30%、陰離子系分散劑65%、水分5%所構成之染料調合物[1-1]。30 parts of the dye represented by the above formula [1-1], 35 parts of the formaldehyde condensate of naphthalenesulfonic acid and 85 parts of water, micronized by a sand mill, and then added 30 parts of lignosulfonic acid, and then obtained The mixture was spray-dried to obtain a dye blend [1-1] composed of 30% of the dye represented by the formula [1-1], 65% of an anionic dispersant, and 5% of water.
除使用上述式[1-2]所表示之染料取代上述式[1-1]所表示之染料之外,與實施例4以相同方式製得染料30%、陰離子系分散劑65%、水分5%所構成之染料調合物[1-2]。A dye 30%, an anionic dispersant 65%, and a moisture content 5 were obtained in the same manner as in Example 4 except that the dye represented by the above formula [1-2] was used instead of the dye represented by the above formula [1-1]. % of the dye composition [1-2].
除使用上述式[1-3]所表示之染料取代上述式[1-1]所表示之染料之外,與實施例4以相同方式製得染料30%、陰離子系分散劑65%、水分5%所構成之染料調合物[1-3]。A dye 30%, an anionic dispersant 65%, and a moisture content 5 were produced in the same manner as in Example 4 except that the dye represented by the above formula [1-3] was used in place of the dye represented by the above formula [1-1]. % of the dye composition [1-3].
除取代上述式[1-1]所表示之染料,而使用上述式[2]所表示之染料、上述式[3]所表示之染料、上述式[4-1]所表示之染料、上述式[4-2]所表示之染料、上述式[4-3]所表示之染料、上述式[5]所表示之染料、上述式[6-1]所表示之染料、上述式[6-2]所表示之染料、上述式[7]所表示之染料、上述式[8-1]所表示之染料、上述式[8-2]所表示之染料、上述式[8-3]所表示之染料、上述式[9]所表示之染料、上述式[10-1]所表示之染料、上述式[10-2]所表示之染料、上述式[11-1]所表示之染料、上述式[12]所表示之染料、上述式[13-1]所表示之染料、上述式[14]所表示之染料、上述式[15-1]所表示之染料、上述式[15-2]所表示之染料、上述式[15-3]所表示之染料、上述式[16-1]所表示之染料及上述式[16-2]所表示之染料以外,與實施例4以相同方式分別製得染料30%、陰離子系分散劑65%、水分5%所構成之染料調合物[2]、染料調合物[3]、染料調合物[4-1]、染料調合物[4-2]、染料調合物[4-3]、染料調合物[5]、染料調合物[6-1]、染料調合物[6-2]、染料調合物[7]、染料調合物[8-1]、染料調合物[8-2]、染料調合物[8-3]、染料調合物[9]、染料調合物[10-1]、染料調合物[10-2]、染料調合物[11-1]、染料調合物[12]、染料調合物[13-1]、染料調合物[14]、染料調合物[15-1]、染料調合物[15-2]、染料調合物[15-3]、染料調合物[16-1]及染料調合物[16-2]。In addition to the dye represented by the above formula [1-1], the dye represented by the above formula [2], the dye represented by the above formula [3], the dye represented by the above formula [4-1], and the above formula are used. [4-2] The dye represented by the above formula [4-3], the dye represented by the above formula [5], the dye represented by the above formula [6-1], and the above formula [6-2] The dye represented by the above formula [7], the dye represented by the above formula [8-1], the dye represented by the above formula [8-2], and the formula [8-3] The dye, the dye represented by the above formula [9], the dye represented by the above formula [10-1], the dye represented by the above formula [10-2], the dye represented by the above formula [11-1], and the above formula [12] The dye represented by the above formula [13-1], the dye represented by the above formula [14], the dye represented by the above formula [15-1], and the above formula [15-2] The dye represented by the above formula [15-3], the dye represented by the above formula [16-1], and the dye represented by the above formula [16-2] are produced in the same manner as in the fourth embodiment. Dye 30%, anionic Dye blending compound [2], dye blending compound [3], dye blending compound [4-1], dye blending compound [4-2], dye blending compound [4-3] composed of 65% and 5% moisture , dye blends [5], dye blends [6-1], dye blends [6-2], dye blends [7], dye blends [8-1], dye blends [8-2] , dye blends [8-3], dye blends [9], dye blends [10-1], dye blends [10-2], dye blends [11-1], dye blends [12] , dye blend [13-1], dye blend [14], dye blend [15-1], dye blend [15-2], dye blend [15-3], dye blend [16- 1] and dye blends [16-2].
除取代上述式[1-1]所表示之染料,而使用上述式(1)所表示之染料、上述式(2)所表示之染料、下述式(3-1)所表示之染料、上述式(4)所表示之染料及上述式(3)所表示之染料以外,與實施例4以相同方式分別製得染料30%、陰離子系分散劑65%、水分5%所構成之染料調合物(1)、染料調合物(2)、染料調合物(3-1)、染料調合物(4)及染料調合物(3)。其中,上述式(3)所表示之染料,係與上述式[17]所表示之染料為相同染料,於實施例之配合例中亦取代式[17]而以式(3)表示。In addition to the dye represented by the above formula [1-1], the dye represented by the above formula (1), the dye represented by the above formula (2), the dye represented by the following formula (3-1), and the above A dye composition composed of a dye represented by the formula (4) and a dye represented by the above formula (3) in the same manner as in Example 4, wherein a dye 30%, an anionic dispersant 65%, and 5% moisture were respectively obtained. (1), dye blend (2), dye blend (3-1), dye blend (4), and dye blend (3). In addition, the dye represented by the above formula (3) is the same dye as the dye represented by the above formula [17], and is represented by the formula (3) in place of the formula [17] in the compounding examples of the examples.
又,下述式(3-1)所表示之染料,係除使用1-甲基-2-苯基吲哚取代N-氰乙基-N-苯甲醯氧乙苯胺以外,與實施例1以相同方式製得。Further, the dye represented by the following formula (3-1) is the same as Example 1 except that 1-methyl-2-phenylindole is substituted for N-cyanoethyl-N-benzamide. Made in the same way.
於染色用槽置入上述染色調合物[1-1](0.58g)(染料份0.174g)與水300cc,將該混合物之pH使用乙酸調整為pH5,製得染色浴。接著,於上述染色用槽中之染色浴投入普通聚酯織物商品名「德羅比卡魯」(帝人(股)製)(15g),以130℃染色40分鐘。之後,以一般方法將該織物還原洗淨,之後進行乾燥,製得染色物A[1-1]。將所得之染色物視為染色濃度1/1N之染色布。The dyeing mixture [1-1] (0.58 g) (dye fraction 0.174 g) and water 300 cc were placed in a dyeing tank, and the pH of the mixture was adjusted to pH 5 using acetic acid to prepare a dyeing bath. Next, the dyeing bath in the above-mentioned dyeing tank was put into a general polyester fabric trade name "Drobikaru" (manufactured by Teijin Co., Ltd.) (15 g), and dyed at 130 ° C for 40 minutes. Thereafter, the fabric was reduced and washed in a usual manner, followed by drying to obtain a dye A [1-1]. The obtained dyed matter was regarded as a dyed cloth having a dyeing concentration of 1/1 N.
除使用上述染料調合物[1-2]0.58g(染料份0.174g)及上述染料調合物[1-3]0.58g(染料份0.174g)取代該染料調合物[1-1]以外,與實施例6以相同方式分別進行染色,製得染色物A[1-2]及染色物A[1-3]。In addition to using the above dye blend [1-2] 0.58 g (dye fraction 0.174 g) and the above dye blend [1-3] 0.58 g (dye fraction 0.174 g) in place of the dye blend [1-1], Example 6 was separately dyed in the same manner to obtain a dye A [1-2] and a dye A [1-3].
除取代上述染料調合物[1-1],使用上述染料調合物(1)(0.58g)(染料份0.174g)、上述染料調合物(2)(0.58g)(染料份0.174g)、上述染料調合物(3-1)(0.58g)(染料份0.174g)、上述染料調合物(4)(0.58g)(染料份0.174g)及上述染料調合物(3)(0.58g)(染料份0.174g)以外,與實施例6同樣地分別進行染色,製得染色物A(1)、染色物A(2)、染色物A(3-1)、染色物A(4)及染色物A(3)。In addition to the above dye blend [1-1], the above dye blend (1) (0.58 g) (dye fraction 0.174 g), the above dye blend (2) (0.58 g) (dye fraction 0.174 g), the above Dye blending compound (3-1) (0.58 g) (dye fraction 0.174 g), the above dye blending compound (4) (0.58 g) (dye fraction 0.174 g) and the above dye blending compound (3) (0.58 g) (dye) In the same manner as in Example 6, except that 0.174 g of the compound was used, dyeing was carried out to obtain a dye A (1), a dye A (2), a dye A (3-1), a dye A (4), and a dyed product. A (3).
對實施例6及7以及比較例2所得之染色物,測定耐光堅牢度、昇華堅牢度及吸盡率(上色染深性),其結果示於表1。又,所使用之各染料之丙酮溶液之最大吸收波長(λm a x )亦記載於表1。The dyes obtained in Examples 6 and 7 and Comparative Example 2 were measured for light fastness, sublimation fastness, and exhaustion rate (dye staining), and the results are shown in Table 1. Further, the maximum absorption wavelength (λ m a x ) of the acetone solution of each dye used is also shown in Table 1.
[耐光堅牢度]耐光堅牢度,係使用染色濃度1/1N之染色布,根據JIS L 0842-1996,以紫外線碳弧燈法,使用紫外線褪色試驗機(Fade-o-meter)U 48(斯卡試驗機(股)製),試驗裝置內之溫度,係使裝置內所收納之稱為黑面板之基準板的溫度為63±3℃之方式保持,照射80小時後,以JIS L 0804-1994變褪色用灰度標(對應國際規格:ISO 105-A02)判定。[Light fastness] Light fastness is a dyed fabric with a dyeing concentration of 1/1 N. According to JIS L 0842-1996, a UV-carbon arc lamp method is used, and a Fade-o-meter U 48 is used. The temperature of the test device is maintained in such a manner that the temperature of the reference plate called the black panel stored in the device is 63 ± 3 ° C. After 80 hours of irradiation, JIS L 0804- In 1994, the fading was judged by the gray scale (corresponding to the international standard: ISO 105-A02).
[昇華堅牢度]昇華堅牢度,係使用染色濃度1/1N之染色布,根據JIS L 0879-1996(對應國際規格:ISO 105-P01:1993),以處理溫度180±2℃×30秒(添加污染布=東雷(股)製聚酯商品名「鐵得隆」及尼龍)進行。[Sublimation fastness] Sublimation fastness, using a dyeing cloth with a dyeing concentration of 1/1N, according to JIS L 0879-1996 (corresponding to international specifications: ISO 105-P01: 1993), with a processing temperature of 180 ± 2 ° C × 30 seconds ( Add contaminated cloth = Donglei (share) polyester product name "Tie Delong" and nylon).
[吸盡性(上色染深性)]吸盡性(染色性),係比較染色濃度1/2N、1/1N、2/1N並以目視判定。◎指「非常良好」、○指「良好」、△指「稍差」、×指「差」之意。[Exhaustion (coloring and dyeing)] Exhaustion (dyeability), the dyeing concentrations were 1/2 N, 1/1 N, 2/1 N, and visually determined. ◎ means "very good", ○ means "good", △ means "slightly worse", and × means "poor".
【表1】表1:染色物為普通聚酯布時之堅牢度及各染料之λm a x
由表1可知,使用普通聚酯布之染色物中,關於本發明之式[1]所表示之橙色分散性染料,耐光堅牢度為4-5級、昇華堅牢度為3-4級以上、上色染深性亦良好,耐光性、昇華堅牢度及上色染深性優異。另一方面,關於比較例之上述式(1)所表示之染料及上述式(2)所表示之染料,昇華堅牢度及上色染深性雖優異,但耐光性為4級,較本發明之橙色分散性染料稍差。又,上述式(3-1)所表示之染料,耐光性係與本發明之橙色分散性染料同等級而為優異,但昇華堅牢度差至2級,上色染深性亦不佳。又,上述式(4)所表示之染料,耐光性及上色染深性雖優異,但昇華堅牢度差至3級。又,上述式(3)所表示之染料,耐光性雖非常優異,但昇華堅牢度差至3級,且上色染深性亦不佳。As is clear from Table 1, the orange disperse dye represented by the formula [1] of the present invention has a light fastness of 4 to 5 and a sublimation fastness of 3-4 or more. It is also dyed with good dyeing, excellent light fastness, sublimation fastness and color dyeing. On the other hand, the dye represented by the above formula (1) of the comparative example and the dye represented by the above formula (2) are excellent in sublimation fastness and color dyeing, but have light resistance of 4 grades, compared with the present invention. The orange disperse dye is slightly worse. Further, the dye represented by the above formula (3-1) is excellent in light resistance in the same level as the orange disperse dye of the present invention, but the sublimation fastness is inferior to 2 grades, and the dyeing depth is also poor. Further, the dye represented by the above formula (4) is excellent in light resistance and coloration, but has a sublimation fastness of 3 grades. Further, the dye represented by the above formula (3) is excellent in light resistance, but the sublimation fastness is poor to three grades, and the dyeing depth is also poor.
又,本發明之橙色分散性染料,與式(1)所表示之染料、式(2)所表示之染料、式(3-1)所表示之染料、式(3)所表示之染料相比,由於λm a x 為長波長側,故可知呈現稍微帶紅色之色相。Further, the orange dispersible dye of the present invention is compared with the dye represented by the formula (1), the dye represented by the formula (2), the dye represented by the formula (3-1), and the dye represented by the formula (3). Since λ m a x is on the long wavelength side, it is known that a hue is slightly reddish.
於染色用槽置入上述染料調合物[1-1](0.28g)(染料份0.084g)與水300cc,將該混合物之pH使用乙酸調整為pH5,製得染色浴。接著,於上述染色用槽中之染色浴投入纖度0.3丹之新合纖(細丹尼聚酯纖維)(15g),以130℃染色40分鐘。之後,以一般方法將該新合纖還原洗淨,之後進行乾燥,製得橙色之染色物B[1-1]。To the dyeing tank, the above dye blend [1-1] (0.28 g) (dye fraction 0.084 g) and water 300 cc were placed, and the pH of the mixture was adjusted to pH 5 using acetic acid to prepare a dye bath. Next, a new synthetic fiber (fine denier polyester fiber) (15 g) having a fineness of 0.3 dan was placed in the dyeing bath in the above dyeing tank, and dyed at 130 ° C for 40 minutes. Thereafter, the new synthetic fiber was reduced and washed in a usual manner, followed by drying to obtain an orange dye B [1-1].
除使用上述染料調合物[1-2](0.28g)(染料份0.084g)及上述染料調合物[1-3](0.28g)(染料份0.084g),取代上述染料調合物[1-1]以外,與實施例8以相同方式分別進行染色,製得染色物B[1-2]及染色物B[1-3]。In place of the above dye blend [1], except the above dye blend [1-2] (0.28 g) (dye fraction 0.084 g) and the above dye blend [1-3] (0.28 g) (dye fraction 0.084 g) were used. In the same manner as in Example 8, dyeing was carried out in the same manner as in Example 1 to obtain a dye B [1-2] and a dye B [1-3].
除取代上述染料調合物[1-1],分別使用上述染料調合物(1)(0.28g)(染料份0.084g)、上述染料調合物(2)(0.28g)(染料份0.084g)、上述染料調合物(3-1)(0.28g)(染料份o.084g)、上述染料調合物(4)(0.28g)(染料份0.084g)、上述染料調合物(3)(0.28g)(染料份0.084g)以外,與實施例8以相同方式分別進行染色,製得染色物B(1)、染色物B(2)、染色物B(3-1)、染色物B(4)及染色物B(3)。In addition to the above dye blend [1-1], the above dye blend (1) (0.28 g) (dye fraction 0.084 g), the above dye blend (2) (0.28 g) (dye fraction 0.084 g), The above dye blend (3-1) (0.28 g) (dye fraction o.084 g), the above dye blend (4) (0.28 g) (dye fraction 0.084 g), and the above dye blend (3) (0.28 g) (Dye portion 0.084 g), dyeing was carried out in the same manner as in Example 8 to obtain a dye B (1), a dye B (2), a dye B (3-1), and a dye B (4). And dyeing B (3).
除於上述染色用槽中追加苯并***系紫外線吸收劑桑萊夫LPS-950(日華化學(股)製)(0.30g)以外,與實施例8以相同方法將新合纖(細丹尼聚酯纖維)染色,製得橙色之染色物C[1-1]。In the same manner as in Example 8, a new synthetic fiber (fine) was added in the same manner as in Example 8 except that a benzotriazole-based ultraviolet absorber, Sanlev LPS-950 (manufactured by Nikko Chemical Co., Ltd.) (0.30 g) was added to the dyeing tank. Danny polyester fiber was dyed to obtain an orange dye C [1-1].
除使用上述染料調合物[1-2]及上述染料調合物[1-3]取代上述染料調合物[1-1]以外,與實施例10以相同方式分別進行染色,製得染色物C[1-2]及染色物C[1-3]。Dyeing was carried out in the same manner as in Example 10 except that the above dye blend [1-2] and the above dye blend [1-3] were used in place of the above dye blend [1-1], to obtain a dye C [ 1-2] and dyed substance C [1-3].
除使用上述染料調合物(1)、(2)、(3-1)、(4)及(3)取代上述染料調合物[1-1]以外,與實施例10以相同方式分別進行染色,製得染色物C(1)、染色物C(2)、染色物C(3-1)、染色物C(4)及染色物C(3)。The dyeing was carried out in the same manner as in Example 10 except that the above dye blends (1), (2), (3-1), (4), and (3) were used instead of the above dye blends [1-1]. A dye C (1), a dye C (2), a dye C (3-1), a dye C (4), and a dye C (3) were obtained.
對實施例8~11及比較例3、4所得之染色物B及C,測定耐光堅牢度。耐光堅牢度,係根據較JIS L 0842嚴苛之試驗方法之豐田法進行。具體而言,耐光堅牢度,係於染色布內面糊上聚氨酯泡沫塑料(urethane foam),使用氙弧燈耐候試驗機(黑面板溫度73±3℃,放射照度150W/m2 ,斯卡試驗機(股)製,超級氙弧燈耐候試驗機SC750)照射明暗38循環後,以JIS L 0804變褪色用灰度標判定。For the dyes B and C obtained in Examples 8 to 11 and Comparative Examples 3 and 4, the light fastness was measured. The light fastness is based on the Toyota method which is more stringent than JIS L 0842. Specifically, the light fastness is based on the urethane foam on the batter in the dyed fabric, and the Xenon arc lamp weathering test machine is used (black panel temperature 73±3°C, irradiance 150W/m 2 , ska test machine) (Stock) system, super xenon arc lamp weathering test machine SC750) After the light and dark 38 cycles, the fading of JIS L 0804 was judged by gray scale.
耐光堅牢度之測定所使用之上述豐田法,係豐田汽車股份有限公司之試驗規格,係以氙弧(氙氣燈)做為光源進行,而以纖維、塑膠做為試驗對象。於試驗,一般係使用稱為氙弧燈耐候試驗機之試驗裝置。此處,將光源之照射強度設為150W/m2 (波長300~400nm),該照射方法,為明暗法,亦即照射既定時間後停止照射既定時間使其變暗,反覆此操作來進行。具體而言,將照射時間3.8小時及暗時間1小時做為1循環,進行38循環(約182小時)。試驗裝置內之(試驗環境氣氛之)濕度,於照射中保持50±5%、暗時間中保持95±5%。又,試驗裝置內之溫度,係使裝置內所收納之稱為黑面板之基準板的溫度為73±3℃之方式保持。收納於裝置內進行試驗之試驗布(纖維),係於內面糊上聚氨酯泡沫塑料。The above-mentioned Toyota method used for the measurement of light fastness is the test specification of Toyota Motor Corporation, which uses xenon arc (xenon lamp) as a light source, and fiber and plastic as test objects. For the test, a test device called a xenon arc lamp weathering tester is generally used. Here, the irradiation intensity of the light source is set to 150 W/m 2 (wavelength: 300 to 400 nm), and the irradiation method is performed by a light-dark method, that is, after a predetermined period of time, the irradiation is stopped for a predetermined period of time to be darkened, and the operation is repeated. Specifically, the irradiation time was 3.8 hours and the dark time was 1 hour as 1 cycle, and 38 cycles (about 182 hours) were performed. The humidity in the test apparatus (at the test atmosphere) was maintained at 50 ± 5% during irradiation and 95 ± 5% during dark time. Further, the temperature in the test apparatus was maintained such that the temperature of the reference plate called the black panel accommodated in the apparatus was 73 ± 3 °C. The test cloth (fiber) stored in the apparatus for testing was attached to the inner surface of the polyurethane foam.
實施例8~11及比較例3、4所得之染色物B及C,以上述方法所測定之耐光堅牢度,係如以下所示。染色物B[1-1]為4+ 、染色物B[1-2]為4、染色物B[1-3]為4、染色物C[1-1]為4-5、染色物C[1-2]為4+ 、染色物C[1-3]為4+ 、染色物B(1)為3、染色物B(2)為3-4、染色物B(3-1)為4+ 、染色物B(4)為3-4、染色物B(3)為4+ 、染色物C(1)為3-4、染色物C(2)為3-4、染色物C(3-1)為4-5、染色物C(4)為4、染色物C(3)為4-5。上述結果,亦示於以下之表2。The light fastness measured by the above methods for the dyes B and C obtained in Examples 8 to 11 and Comparative Examples 3 and 4 is as follows. The dye B [1-1] is 4 + , the dye B [1-2] is 4, the dye B [1-3] is 4, the dye C [1-1] is 4-5, and the dye C is [1-2] is 4 + , the dyeing substance C[1-3] is 4 + , the dyeing substance B (1) is 3, the dyeing substance B (2) is 3-4, and the dyeing substance B (3-1) is 4 + , dye B (4) is 3-4, dye B (3) is 4 + , dye C (1) is 3-4, dye C (2) is 3-4, dye C ( 3-1) is 4-5, the dye C(4) is 4, and the dye C(3) is 4-5. The above results are also shown in Table 2 below.
由表2可知,於豐田法之使用細丹尼聚酯纖維之染色物之耐光性試驗,本發明之式[1]所表示之橙色分散性染料,耐光堅牢度為4級以上為優異,特別是上述式[1-1]所表示之染料,耐光性非常優異。另一方面,上述式(1)所表示之染料及上述式(2)所表示之染料,耐光堅牢度為3-4以下而稍差,紫外線吸收劑之效果亦小。又,上述式(3-1)所表示之染料及上述式(3)所表示之染料,耐光性非常優異。又,上述式(4)所表示之染料,與本發明之染料相比,耐光性稍差。As can be seen from Table 2, the orange disperse dye represented by the formula [1] of the present invention is excellent in light fastness of 4 or more, particularly in the light resistance test of the dye of the fine denier polyester fiber. It is a dye represented by the above formula [1-1] and is excellent in light resistance. On the other hand, the dye represented by the above formula (1) and the dye represented by the above formula (2) have a light fastness of 3-4 or less and a slight effect, and the effect of the ultraviolet absorber is also small. Further, the dye represented by the above formula (3-1) and the dye represented by the above formula (3) are extremely excellent in light resistance. Further, the dye represented by the above formula (4) is slightly inferior in light resistance to the dye of the present invention.
因此,由表1及表2可知,本發明之橙色分散性染料,耐光性、昇華堅牢度及上色染深性優異,上述式[1-1]所表示之染料,耐光性特別優異。另一方面,上述式(1)所表示之染料及上述式(2)所表示之染料,昇華堅牢度及上色染深性雖優異,但耐光性較本發明之橙色分散性染料差,特別以豐田法時為明顯。又,上述式(3-1)所表示之染料及上述式(3)所表示之染料,雖耐光性非常優異,但昇華堅牢度差、上色染深性亦不佳。又,上述式(4)所表示之染料,上色染深性雖優異,但昇華堅牢度差,且使用豐田法之耐光堅牢度亦差。Therefore, the orange disperse dye of the present invention is excellent in light resistance, sublimation fastness, and coloring dyeing property, and the dye represented by the above formula [1-1] is particularly excellent in light resistance. On the other hand, the dye represented by the above formula (1) and the dye represented by the above formula (2) are excellent in sublimation fastness and color dyeing, but are inferior to the orange disperse dye of the present invention, particularly It is obvious when the Toyota Law is used. Further, the dye represented by the above formula (3-1) and the dye represented by the above formula (3) are excellent in light resistance, but the sublimation fastness is poor and the dyeing depth is also poor. Further, the dye represented by the above formula (4) is excellent in color dyeing, but has poor sublimation fastness and poor light fastness by using the Toyota method.
將上述染料調合物[1-1]、上述染料調合物[1-2]、上述染料調合物[1-3]、染料調合物[2]、染料調合物[3]、染料調合物[4-1]、染料調合物[4-2]、染料調合物[4-3]、染料調合物[5]、染料調合物[6-1]、染料調合物[6-2]、染料調合物[7]、染料調合物[8-1]、染料調合物[8-2]、染料調合物[8-3]、染料調合物[9]、染料調合物[10-1]、染料調合物[10-2]、染料調合物[11-1]、染料調合物[12]、染料調合物[13-1]、染料調合物[14]、染料調合物[15-1]、染料調合物[15-2]、染料調合物[15-3]、染料調合物[16-1]及染料調合物[16-2]、及上述染料調合物(3),以下述表3~表5所示比例(重量份)配合,調製成分散性染料組成物1~26。The above dye blend [1-1], the above dye blend [1-2], the above dye blend [1-3], dye blend [2], dye blend [3], dye blend [4] -1], dye blend [4-2], dye blend [4-3], dye blend [5], dye blend [6-1], dye blend [6-2], dye blend [7], dye blend [8-1], dye blend [8-2], dye blend [8-3], dye blend [9], dye blend [10-1], dye blend [10-2], dye blend [11-1], dye blend [12], dye blend [13-1], dye blend [14], dye blend [15-1], dye blend [15-2], dye blend [15-3], dye blend [16-1] and dye blend [16-2], and the above dye blend (3), as shown in Tables 3 to 5 below. The ratio (parts by weight) was blended to prepare a disperse dye composition 1 to 26.
於染色用槽置入各染料調合物(0.28g)(染料份0.084g)、水(300cc)與苯并***系紫外線吸收劑桑萊夫LPS-950(日華化學(股)製)(0.30g),將該混合物之pH使用乙酸調整為pH5,製得染色浴。接著,於上述染色用槽中之染色浴投入實施例8所使用之新合纖織物(細丹尼聚酯纖維)15g,以130℃染色40分鐘。之後,以一般方法將該新合纖織物還原洗淨,之後進行乾燥,分別製得染色物D。對所製得之染色物D,與染色物B及C以相同方式測定耐光堅牢度之結果,顯示良好之耐光堅牢度。Each dye blend (0.28 g) (dye fraction 0.084 g), water (300 cc) and benzotriazole-based UV absorber Sanlev LPS-950 (made by Rihua Chemical Co., Ltd.) were placed in the dyeing tank ( 0.30 g), the pH of the mixture was adjusted to pH 5 using acetic acid to prepare a dye bath. Next, 15 g of a new synthetic fiber fabric (fine denier polyester fiber) used in Example 8 was placed in the dyeing bath in the above dyeing tank, and dyed at 130 ° C for 40 minutes. Thereafter, the new synthetic fabric was subjected to reduction washing in a usual manner, followed by drying to obtain a dye D, respectively. As a result of measuring the light fastness of the dye D obtained in the same manner as the dyes B and C, good light fastness was exhibited.
以下,說明噴墨印染用墨水之調製方法。Hereinafter, a method of preparing ink for inkjet printing will be described.
於含有上述式[1-1]所表示之染料(20份)、做為分散劑之陰離子性界面活性劑之特殊芳香族磺酸鈉之甲醛縮合物(花王(股)製,商品名「德摩魯SNB」)(10份)、「攸尼德克斯480」(美國貝德羅萊特公司製,相當於上述化學式(I)之化合物之R為碳數30之直鏈烷基,n為約40,HLB=16者)(3份)、水(127份)之混合物,使用直徑0.4mm之鋯石珠(330份),以砂磨機進行微粒子化35小時,製得染料濃度12.5%之墨水用分散液[1-1]。該染料之平均粒徑為0.10μm。A formaldehyde condensate of a special aromatic sodium sulfonate containing a dye (20 parts) represented by the above formula [1-1] and an anionic surfactant as a dispersing agent (King, manufactured by Kao) Moru SNB") (10 parts), "Monidox 480" (manufactured by Bedrolet, USA, equivalent to the compound of the above formula (I), R is a linear alkyl group having a carbon number of 30, n is A mixture of about 40, HLB = 16) (3 parts) and water (127 parts), using zircon beads (330 parts) having a diameter of 0.4 mm, was micronized by a sand mill for 35 hours to obtain a dye concentration of 12.5%. The ink dispersion [1-1]. The dye had an average particle diameter of 0.10 μm.
除使用上述式[1-2](20份)所表示之染料取代上述式[1-1]所表示之染料以外,與墨水用分散液[1-1]以相同方式製得染料濃度12.5%之墨水用分散液[1-2]。該染料之平均粒徑為0.10μm。A dye concentration of 12.5% was prepared in the same manner as the ink dispersion [1-1] except that the dye represented by the above formula [1-2] (20 parts) was used instead of the dye represented by the above formula [1-1]. The ink dispersion [1-2]. The dye had an average particle diameter of 0.10 μm.
除使用上述式[3](20份)所表示之染料取代上述式[1-1]所表示之染料以外,與墨水用分散液[1-1]以相同方式製得染料濃度12.5%之墨水用分散液[3]。該染料之平均粒徑為0.10μm。An ink having a dye concentration of 12.5% was prepared in the same manner as the ink dispersion [1-1] except that the dye represented by the above formula [3] (20 parts) was used instead of the dye represented by the above formula [1-1]. Use dispersion [3]. The dye had an average particle diameter of 0.10 μm.
除使用上述式[4-3](20份)所表示之染料取代上述式 [1-1]所表示之染料以外,與墨水用分散液[1-1]以相同方式製得染料濃度12.5%之墨水用分散液[4-3]。該染料之平均粒徑為0.10μm。Substituting the above formula using the dye represented by the above formula [4-3] (20 parts) In the same manner as the ink dispersion [1-1], an ink dispersion [4-3] having a dye concentration of 12.5% was prepared in the same manner as the dye represented by [1-1]. The dye had an average particle diameter of 0.10 μm.
除使用上述式[5](20份)所表示之染料取代上述式[1-1]所表示之染料以外,與墨水用分散液[1-1]以相同方式製得染料濃度12.5%之墨水用分散液[5]。該染料之平均粒徑為0.10μm。An ink having a dye concentration of 12.5% was prepared in the same manner as the ink dispersion [1-1] except that the dye represented by the above formula [5] (20 parts) was used instead of the dye represented by the above formula [1-1]. Use dispersion [5]. The dye had an average particle diameter of 0.10 μm.
除使用上述式[8-3](20份)所表示之染料取代上述式[1-1]所表示之染料以外,與墨水用分散液[1-1]以相同方式製得染料濃度12.5%之墨水用分散液[8-3]。該染料之平均粒徑為0.10μm。A dye concentration of 12.5% was obtained in the same manner as the ink dispersion [1-1] except that the dye represented by the above formula [8-3] (20 parts) was used instead of the dye represented by the above formula [1-1]. The ink dispersion [8-3]. The dye had an average particle diameter of 0.10 μm.
除使用上述式[12](20份)所表示之染料取代上述式[1-1]所表示之染料以外,與墨水用分散液[1-1]以相同方式製得染料濃度12.5%之墨水用分散液[12]。該染料之平均粒徑為0.10μm。An ink having a dye concentration of 12.5% was prepared in the same manner as the ink dispersion [1-1] except that the dye represented by the above formula [12] (20 parts) was used instead of the dye represented by the above formula [1-1]. Use dispersion [12]. The dye had an average particle diameter of 0.10 μm.
除使用上述式[13-1](20份)所表示之染料取代上述式[1-1]所表示之染料以外,與墨水用分散液[1-1]以相同方式製得染料濃度12.5%之墨水用分散液[13-1]。該染料之平均粒徑為0.10μm。A dye concentration of 12.5% was prepared in the same manner as the ink dispersion [1-1] except that the dye represented by the above formula [13-1] (20 parts) was used instead of the dye represented by the above formula [1-1]. The ink dispersion [13-1]. The dye had an average particle diameter of 0.10 μm.
以下,說明黑墨水之例,其配合比例係示於表6。Hereinafter, an example of black ink will be described, and the mixing ratio thereof is shown in Table 6.
於墨水用分散液[1-1](56份)、墨水用分散液[12](84份)及墨水用分散液[13-1](84份)之混合液,添加水溶性有機溶劑之甘油(100份)及表面調整劑之聚醚變性聚二甲基矽氧烷(畢克化藥日本(股)製,商品名「BYK-348」)(1.0份),並對其添加水使總量為400份,以將染料濃度調整成7%,而製成墨水。各染料之重量比例,係式[1-1]所表示之染料:式[2]所表示之染料:式[13-1]所表示之染料=25:37.5:37.5。A water-soluble organic solvent is added to a mixture of the ink dispersion [1-1] (56 parts), the ink dispersion [12] (84 parts), and the ink dispersion [13-1] (84 parts). Glycerol (100 parts) and a surface-adjusting agent polyether-denatured polydimethylsiloxane (manufactured by Biek Chemical Co., Ltd., trade name "BYK-348") (1.0 parts), and added with water The total amount was 400 parts to adjust the dye concentration to 7% to prepare an ink. The dye ratio represented by the formula [1-1]: the dye represented by the formula [2]: the dye represented by the formula [13-1] = 25:37.5:37.5.
於墨水用分散液[1-2](40份)、墨水用分散液[3](18份)、墨水用分散液[8-3](11份)、墨水用分散液[12](67份)及墨水用分散液[13-1](88份)之混合液,添加水溶性有機溶劑之甘油(100份)及表面調整劑之商品名「BYK-348」(畢克化藥日本(股)製,)(1.0份),並對其添加水使總量為400份,以將染料濃度調整成7%,而製成墨水。各染料之重量比例,係式[1-2]所表示之染料:式[3]所表示之染料:式[8-3]所表示之染料:式[12]所表示之染料:式[13-1]所表示之染料=18:8:5:30:39。Ink dispersion [1-2] (40 parts), ink dispersion [3] (18 parts), ink dispersion [8-3] (11 parts), ink dispersion [12] (67) And a mixture of the ink dispersion [13-1] (88 parts), a glycerin (100 parts) containing a water-soluble organic solvent, and a surface conditioner "BYK-348" (Biek Chemical Japan) The system was made, (1.0 parts), and water was added thereto so that the total amount was 400 parts, and the dye concentration was adjusted to 7% to prepare an ink. The dye ratio represented by the formula [1-2]: the dye represented by the formula [3]: the dye represented by the formula [8-3]: the dye represented by the formula [12]: the formula [13] The dye represented by -1] = 18:8:5:30:39.
以下說明橙色墨水之例,其配合比例係示於表7。An example of an orange ink will be described below, and the mixing ratio thereof is shown in Table 7.
於墨水用分散液[1-1](101份)及墨水用分散液[3](43份)之混合液,添加做為分散劑之商品名「德摩魯SNB」(花王(股)製)之10%水溶液(40份)、水溶性有機溶劑之甘油(110份)及表面調整劑之商品名「BYK-348」(畢克化藥日本(股)製,)(1.0份),並對其添加水使總量為400份,以將染料濃度調整成4.5%,而製成墨水。各染料之重量比例,係式[1-1]所表示之染料:式[3]所表示之染料=70:30。In the mixture of the ink dispersion [1-1] (101 parts) and the ink dispersion [3] (43 parts), the product name "Demoru SNB" (King) is added as a dispersing agent. ) a 10% aqueous solution (40 parts), a glycerin (110 parts) of a water-soluble organic solvent, and a surface conditioner of "BYK-348" (made by Biek Chemicals Japan Co., Ltd.) (1.0 parts), and Water was added thereto so that the total amount was 400 parts to adjust the dye concentration to 4.5% to prepare an ink. The weight ratio of each dye is a dye represented by the formula [1-1]: the dye represented by the formula [3] = 70:30.
於墨水用分散液[1-1](94份)及墨水用分散液[4-3](50份)之混合液,添加做為分散劑之商品名「德摩魯SNB」(花王(股)製)之10%水溶液(40份)、水溶性有機溶劑之甘油(110份)及表面調整劑之商品名「BYK-348」(畢克化藥日本(股)製,)(1.0份),並對其添加水使總量為 400份,以將染料濃度調整成4.5%,而製成墨水。各染料之重量比例,係式[1-1]所表示之染料:式[4-3]所表示之染料=65:35。For the ink dispersion [1-1] (94 parts) and the ink dispersion [4-3] (50 parts), add the product name "Demoru SNB" as a dispersant (Kao) 10% aqueous solution (40 parts) of the system), glycerin (110 parts) of the water-soluble organic solvent, and the trade name "BYK-348" of the surface conditioner (made by Biek Chemicals Japan Co., Ltd.) (1.0 part) And add water to it to make the total 400 parts were prepared to adjust the dye concentration to 4.5% to prepare an ink. The weight ratio of each dye is a dye represented by the formula [1-1]: the dye represented by the formula [4-3] = 65:35.
於墨水用分散液[1-1](101份)及墨水用分散液[5](43份)之混合液,添加做為分散劑之商品名「德摩魯SNB」(花王(股)製)之10%水溶液(40份)、水溶性有機溶劑之甘油(110份)及表面調整劑之商品名「BYK-348」(畢克化藥日本(股)製,)(1.0份),並對其添加水使總量為400份,以將染料濃度調整成4.5%,而製成墨水。各染料之重量比例,係式[1-1]所表示之染料:式[5]所表示之染料=70:30。In the mixture of the ink dispersion [1-1] (101 parts) and the ink dispersion [5] (43 parts), the product name "Demoru SNB" (made by Kao) is added as a dispersing agent. ) a 10% aqueous solution (40 parts), a glycerin (110 parts) of a water-soluble organic solvent, and a surface conditioner of "BYK-348" (made by Biek Chemicals Japan Co., Ltd.) (1.0 parts), and Water was added thereto so that the total amount was 400 parts to adjust the dye concentration to 4.5% to prepare an ink. The weight ratio of each dye is a dye represented by the formula [1-1]: the dye represented by the formula [5] = 70:30.
於墨水用分散液[1-1](89份)及墨水用分散液[6-1](55份)之混合液,添加做為分散劑之商品名「德摩魯SNB」(花王(股)製)之10%水溶液(40份)、水溶性有機溶劑之甘油(110份)及表面調整劑之商品名「BYK-348」(畢克化藥日本(股)製,)(1.0份),並對其添加水使總量為400份,以將染料濃度調整成4.5%,而製成墨水。各染料之重量比例,係式[1-1]所表示之染料:式[6-1]所表示之染料=62:38。For the ink dispersion [1-1] (89 parts) and the ink dispersion [6-1] (55 parts), add the product name "Demoru SNB" as a dispersant (Kao) 10% aqueous solution (40 parts) of the system), glycerin (110 parts) of the water-soluble organic solvent, and the trade name "BYK-348" of the surface conditioner (made by Biek Chemicals Japan Co., Ltd.) (1.0 part) And adding water to the total amount of 400 parts to adjust the dye concentration to 4.5% to prepare an ink. The weight ratio of each dye is a dye represented by the formula [1-1]: the dye represented by the formula [6-1] = 62:38.
分別將上述噴墨印染用墨水[27]~[32]安裝於壓變方式之噴墨印表機,於施以防滲等前處理之1500mm寬×10m長之普通聚酯布上,以列印解析度360×360dpi進行單色、全面印刷。其結果,各噴墨印染用墨水[27]~[32],皆未產生阻塞而顯示良好之噴出安定性。並且,將該聚酯布乾燥後,於175℃之過熱蒸汽中進行熱處理7小時,以將該聚酯布染色。將未固著之染料、分散劑等添加劑及前處理劑等以還原洗淨及水洗除去,進行乾燥,藉此製得各色相之染色物E。以上述豐田法測定所得之染色物E之耐光堅牢度的結果,皆顯示良好之耐光堅牢度。The inkjet printing inks [27] to [32] are respectively mounted on a pressure-sensitive inkjet printer, and are applied to a common polyester cloth of 1500 mm width × 10 m length which is pretreated by an anti-seepage method or the like. The printing resolution is 360×360dpi for monochrome and comprehensive printing. As a result, each of the inkjet inks [27] to [32] showed no clogging and showed good discharge stability. Then, the polyester cloth was dried, and heat-treated in superheated steam at 175 ° C for 7 hours to dye the polyester cloth. An additive such as an unfixed dye or a dispersant, a pretreatment agent, and the like are removed by reduction washing and water washing, and dried to obtain a dyed substance E of each color phase. As a result of measuring the light fastness of the obtained dye E by the above-mentioned Toyota method, it showed good light fastness.
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JP5610910B2 (en) * | 2010-08-06 | 2014-10-22 | 株式会社ミマキエンジニアリング | Printing method |
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CN103228741B (en) * | 2010-11-30 | 2015-07-08 | 日本化药株式会社 | Disperse dyes and method for dyeing hydrophobic fiber material using same |
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JP5817028B2 (en) * | 2011-08-23 | 2015-11-18 | 東洋インキScホールディングス株式会社 | Coloring composition for color filter, and color filter |
KR101416893B1 (en) * | 2012-06-08 | 2014-07-08 | 공명도 | Orange disperse dye composition having excellent moisture resistance |
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CN102827493A (en) * | 2012-09-28 | 2012-12-19 | 吴江市绿洲染料化工有限公司 | Performance-improved disperse blue dye mixture |
CN103073922A (en) * | 2013-01-21 | 2013-05-01 | 江苏亚邦染料股份有限公司 | Orange disperse dye composition |
JP6041152B2 (en) * | 2013-11-13 | 2016-12-07 | セイコーエプソン株式会社 | Inkjet ink composition for sublimation transfer, ink set, and method for producing dyed product |
JP6285281B2 (en) * | 2014-05-30 | 2018-02-28 | セーレン株式会社 | Inkjet ink set, inkjet printing method, and inkjet printed matter |
KR101723853B1 (en) * | 2015-07-09 | 2017-04-07 | 일신교역 주식회사 | Dyes composition for heat transfer printing on nylon fabrics |
TWI561585B (en) * | 2015-12-09 | 2016-12-11 | Ind Tech Res Inst | Dye and dyeing method |
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CN108069875B (en) * | 2016-11-16 | 2021-10-08 | 浙江龙盛化工研究有限公司 | Synthesis process of N-cyanoethyl-N-benzoyloxyethylaniline |
JP6822175B2 (en) * | 2017-01-30 | 2021-01-27 | セイコーエプソン株式会社 | Selection method |
CN107286703B (en) * | 2017-05-26 | 2019-08-20 | 杭州吉华江东化工有限公司 | A kind of high solarization dispersed black dye mixture and its application |
CN107556807B (en) * | 2017-09-18 | 2020-11-03 | 江苏龙达纺织科技有限公司 | Environment-friendly ultra-black dye ink |
KR102060607B1 (en) | 2017-12-29 | 2020-02-11 | 아크로마코리아 주식회사 | The preparing method of disperse orange dye |
KR102116078B1 (en) | 2018-09-18 | 2020-05-28 | 재단법인경북테크노파크 | Manufacturing method of eco-friendly ink for digital priting using natural pigment |
CN109487578A (en) * | 2018-12-04 | 2019-03-19 | 深圳市墨库图文技术有限公司 | Thief zone heat sublimation ink and preparation method thereof |
CN111269586B (en) * | 2020-03-02 | 2021-04-20 | 上海贝通色彩科技有限公司 | Disperse black dye composition, disperse black dye preparation and application thereof |
CN111621167A (en) * | 2020-05-13 | 2020-09-04 | 浙江博澳新材料股份有限公司 | High light fastness type gray-to-black dispersed anthraquinone dye mixture |
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